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Night After Night to @midnight: An oral history of Comedy Central (Part 2)

(Illustration: Nick Wanserski)
(Illustration: Nick Wanserski)

Previously in our oral history of Comedy Central: Comedy kingdoms united, South Park rose, and The Daily Show spoke truth to power. In this installment: Dave Chappelle conquers the world (then abdicates his throne), a visit from the Reno Sheriff’s Department, Stephen Colbert introduces the world to “truthiness,” the Workaholics break out of the internet and Key & Peele break the internet.


2003 was an indelible turning point in Comedy Central’s history. The Daily Show and South Park sparked national conversation and earned critical praise. The Man Show and Crank Yankers drew young male audiences, while Insomniac With Dave Attell and Tough Crowd With Colin Quinn offered comedy geeks insight into professional comedians’ lifestyles and creative processes.

Premium Blend and Comedy Central Presents continued providing the network with branded, largely evergreen, relatively cheap stand-up content. Performers too untested for HBO or edgy for late-night talk scored legit TV credits and exposure to potential fans. “Up until that point it was really just doing a TV spot on a late-night talk show: Letterman or Leno,” recalls Dave Attell of Comedy Central Presents’ late-’90s debut. “That was the first longer-form—23-ish minutes—opportunity newer comics got to do more time. And it was definitely a cooler vibe in terms of pressure. There weren’t the same [content] standards as the networks. Doug Herzog and all his people really liked comedy. They really knew comedy.”

In 2003, former Comedy Central President Herzog was off running USA (and emphasizing the creation of original programming like Monk), but he wouldn’t be gone long. As Win Ben Stein’s Money and Primetime Glick wound down production, the January 22 debut of Chappelle’s Show and July 23 introduction of Reno 911! heralded new watermarks in sketch and improv. That summer Comedy Central also launched what would become one of its most popular (and profitable) franchises, the Comedy Central Roast.

Behind the scenes, 2003 saw another shift. Since 1991’s initial merging of HBO/Time Warner’s The Comedy Channel and MTV Networks/Viacom’s Ha!, both companies had maintained a 50 percent stake in Comedy Central. In April 2003, Viacom bought out Time Warner’s share for $1.23 billion. Herzog would soon return to the Viacom fold along with new Comedy Central President Michele Ganeless (who stepped down from her position in May of 2016), eager to harness the unfettered, streamlined clout of a single parent company.

“When I had been there through the last tour of duty in programming, we had launched Daily Show, South Park, etc., which were still going,” says Ganeless, “But we didn’t have the resources of MTV Networks behind us. So the opportunity to have the strength of MTV Networks behind us was the bigger prevailing feeling. There was a challenge of ‘Okay, what’s next? New hits!’ But nothing more than any other network.”

Their greatest initial challenge, however, became Comedy Central’s single biggest head-scratcher to date: the unexplained disappearance of a game-changing comedian who, ever since he began performing at 14 years old, had defied expectations at every turn.

2003: Chappelle’s Show

“One morning I woke up and somebody said, ‘Dave’s gone. He went to Africa. And no one knows when he’s coming back.’”

Herzog: I knew Dave [Chappelle] before I got back to Comedy Central. I knew him from my original Comedy Central days—maybe even my MTV days.

Lou Wallach (former SVP, original programming and development): We had done a project I was really proud of the year before, on the history of black comedy in America. Dave was interviewed in it. The press department had smartly put together a screening and Q&A for the press in advance of the launch. It was something we were really proud of, like, “Wow, Comedy Central did this?” It was almost too smart. Dave came to the screening and, I believe, hosted it. That sort of opened the door. He was like, “Hey, you guys seem pretty cool, and you did a great job with this.” Based on what I knew of his prior experiences in Hollywood, we felt very different to him than that.

Tony Fox (former EVP of corporate communications): We had invited talent, and he was obviously featured in the documentary. He showed up and just kind of hung out with us. Lou and [Genral Manager] Bill [Hilary] basically got him in a corner and said, “Hey, why don’t you do a show with us? Let’s sit down, figure out some ideas, and see what we can come up with?” And Chappelle’s Show was the result.

Wallach: He was living in Ohio but was in New York a lot, and maybe six months later he came in. There was a meeting that was set up with Bill Hilary’s office, who told me Dave was coming in with his writing partner, Neal Brennan. I don’t even think he set it up through an agent. I’m not even sure he was represented at the time, or not officially. It was Dave, Neal, Bill Hilary, and myself, just the four of us in Bill’s office, at 1775 Broadway. He goes, “I’m basically here to pitch a sketch show, maybe a little variety, and the premise is I want to bring my joke book to life.” He wanted some music and some man-on-the-street stuff, but the basic premise was a sketch show that is Dave Chappelle’s point of view. At the end, Bill said to me, “What do you want to do? Do we develop a script?” It may not have been in the network executive 101 handbook, but in front of Dave I said, “No, we don’t do a script. You have to shoot a pilot. You have to see it. If it’s a joke book come to life, you have to see it.” Bill said, “Okay,” and that was it. We shot a pilot very quickly, maybe eight to 10 weeks later. It was a very small production. Dave and Neal were going to write everything. They were the backbone of the show.

Donnell Rawlings: I met Neal Brennan years ago. He was a PA working for In Living Color, doing the videotaping for auditions, and he became a friend of mine. Dave and Neal wrote Half Baked, and Neal optioned a lot of scripts to Hollywood, but they weren’t getting green-lit. He didn’t just want to get paid; he wanted to see his work in theaters. But nobody knew him as a director, so he wrote a little one-man short and reached out to my manager to ask, “Do you think Donnell would be interested in shooting this?” At the time I didn’t know Neal was already loaded. I said, “Yeah, I’ll find the time to do it. Listen, I know you can’t afford to pay me, but if you’re ever in a situation where you can throw me a bone, I’d appreciate it.” I didn’t think too much of it, but three months later the bone he decided to throw me was Chappelle’s Show.

Herzog: No one’s a bigger fan of Neal than I am. If Dave is Michael Jordan, Neal had to be Scottie Pippen. Scottie Pippen would have been the best player on almost any other team in the NBA. But when the dynamic is that you’re the star of the show and your name’s up there, you’re going to get most of the credit. Or most of the blame. And that comes with the territory. That said, I think Dave has been pretty upfront about Neal’s contributions and how important they were. They were a great team.

Fox: Dave was such a sweet, wonderful, innocent, kind person. His young wife and son used to play in my office when we’d talk about press events and stuff like that.

Wallach: The production office was in Comedy Central, so if he had a question, he would walk up the stairs and sit on my couch. I’d open my window to let him smoke. He and Dave Attell were the only two guys I would let smoke in the office.

Rawlings: It never felt like work. The camaraderie, how much fun we had on set, the way Dave would show love to everyone—not just the leads, but everyone from directors to craft services—everybody felt they were part of the process of making something great.

Fox: Chappelle’s Show was one of the most extraordinary and exciting shows we ever did. And as a PR guy, I’ve got tell you it scared the hell out of me, because it was extremely edgy in terms of it dealing with racial subject matter. I mean, the very first episode had, like, a 12-minute sketch in it, “The Blind Supremacist.”

Wallach: Probably one of my favorites, if not the greatest sketch I’ve ever seen, was “Blind Supremacist,” the two-part Frontline parody. There was a commercial break in between. I remember sitting in my office very shortly before the premiere with Dave and some folks that I worked for. There was an argument: Dave is saying, “Why do we have to make it one segment? It doesn’t work that way.” The answer from the higher-ups was “Because you just don’t do that.” “Why?” “You just don’t do that!” “Well, why?” I said, “It’s the first episode, the third and fourth act. Can we just try it here, and if it doesn’t work, then Dave, you’ll agree that you’ll listen to us?” And he was right. The people I worked under never talked about it again. People wanted to come back from the break and see how it paid off. To cut it down would have been doing a total injustice to the show, to Dave, and to the audience. It’s still some of my favorite sketches to this day. It’s silly, it’s hilariously funny, and it’s totally Dave Chappelle.

Fox: The “Black White Supremacist” was based on a true story and experience that Chappelle’s grandfather had. I forget the whole story, but he was very light-skinned, and he got on a bus where somebody was giving Chappelle’s grandfather shit, like, “Whitey, get outta here!” And he’s going, “Yeah, where’s that white motherfucker?” when they were talking about him.

Kurt Metzger (Inside Amy Schumer staff writer): My first writing job was for Marc Maron’s VH1 show Never Mind The Buzzcocks, and the next thing I did was Chappelle’s Show. I got that through Neal and Dave. It was freelance. It wasn’t an office writing job at all. The only people who really wrote it in the first season were Dave and Neal, and then there was me and Mike Birbiglia and a few other people they bought sketches from. I think I sold them three sketches, but only one of them got to air. I called Neal and asked him if I could submit stuff, and they liked it and called me to buy it. I was so broke at the time, I think Neal wired me $5,000 so I could pay my back rent. The one that made it to air was the Darth Vader/Catholic Church molestation scandal, about Jedis with their little Padawan.

Rawlings: My personal favorite sketch was with Wayne Brady, even though I was only in it a few seconds. At that time I didn’t really have a lot of money. On my days off, I would go to work just so I could mooch off of craft services and get some more experience on-set. So many of the sketches I was in was just because I happened to be hanging around. That Wayne Brady sketch, they didn’t cast me. Neal looked at me and said, “Yo son, you want to get shot up?” How do you refuse to get shot up by Wayne Brady? It was one take: I was in my civilian clothes, my arm really did get caught on that window—it wasn’t part of the scene—they loved it, and it was one of the biggest laughs in that sketch. It was dense, it was funny, it had Wayne Brady being gangster. There was something about watching Wayne Brady with a gun, saying, “Is Wayne Brady gonna have to choke a bitch?” that just took his fan base to the next level.

Keegan-Michael Key (Key & Peele): I got more familiar with Chappelle in the second season. I have to admit that I was a late adopter who then went back and consumed stuff from the first season. I kind of got on the bandwagon with all my friends at MadTV right about the time that the Rick James stuff was coming on. It was like, “But this is crazy! They just gave an entire episode to Charlie, and he gets to talk about Rick James and Prince stories? What is this?” The fact that Dave was given the freedom and the liberty to literally do whatever he wanted to the point where he didn’t even host the show for two episodes in that second season, I thought, “If I had any kind of artistic freedom like that, that would be amazing.”

Rawlings: Now when I go out to dinner with my friends and the check comes, no one even questions who’s going to pay the bill. They just look at me and say, “I thought you was rich, bitch!” When we did that scene, I had an issue with driving the truck. I don’t think I even had a legal driver’s license at the time; nobody asked me. And the street was hot; it wasn’t like we could afford to shut down an entire block in Harlem. So I had to drive this truck up, hit my mark, not run over the reporter, take the keys out of it, and deliver my line. We went through it maybe 10 times, and I couldn’t get it right. Neal looked at me and said, “Donnell, we don’t have all day to do this. You might not be in the scene.” And out of frustration, and being so mad and nervous that I wasn’t going to make it, I was like, “I’m rich, bitch!” And that was the one that stuck.

Larry Wilmore (The Nightly Show): It was an instant classic. I was lucky enough to work on In Living Color, and I always loved The Chris Rock Show. I was so happy there was a show that was doing that kind of satire, and then I was so mad at Chris Rock when it went away. Then I was happy again when Chappelle came on and that kind of humor was being done.

Jordan Peele (Key & Peele): Chappelle’s Show was huge for opening the door for us and other minorities.

Michele Ganeless (former president of Comedy Central): It was a groundbreaking show in the world of sketch. There’s a lot of great sketch comedy shows, but it was singular because Dave’s voice is so singular.

Rawlings: Before Chappelle’s Show, people were fans of Comedy Central—they enjoyed it—but for some reason it seemed like Comedy Central had a cult following. You had to be really into comedy to know about it. I think Chappelle’s Show really took that network to the next level.

Trevor Noah: It was amazing. It was commentary on what was happening. It was the purest form of sketch. It had a rawness and an honesty to it that you really hadn’t seen before. And it was unapologetic. I think that was my favorite thing about it.

Adam DeVine (Workaholics): Chappelle was the apex of comedy. When I first moved out to California, he was still on the air, and was huge, and was just a comedy hero.

Wallach: Between South Park and Dave Chappelle, this was totally going to evolve primetime Comedy Central. And then he left.

Fox: He had a one-year deal with us. If he signed up for two more, retroactively we’d pay him a lot more on the back end, which ultimately meant a great deal of money because seasons one and two both sold about $70 million in DVD sales at retail. So there was a substantial amount of money at stake.

Herzog: I returned to Comedy Central a week or two after season two of Chappelle ended. He was the biggest thing in the world. There was nothing bigger than Dave Chappelle at that point. He had a two-year agreement, but we had no [new] contract with him. So I got back and immediately backed up the truck for Dave Chappelle. I’m the guy who gave him “$50 million,” if that’s what you chose to believe. But I’m the one who gave him the big deal—and it was a big deal. And then I was also the guy who was sitting there when Dave disappeared.

Wallach: I knew something was not great when we kept having to push off production going into season three. We kept postponing delivery dates. We changed the premiere date on the schedule a few times. I didn’t know if it was negotiating thing. The deal had been done; he’d gotten a great deal. There was some stuff leaked in the press about a $50 million deal, which to this day I maintain didn’t come from anybody on the network side. There was nothing to benefit from the network putting it out there. I can only believe that it was put out there by someone on his end. I don’t believe it came from him, either. But right around that time it was like, “This doesn’t feel right.”

Herzog: I would be lying if I said we hadn’t sort of seen evidence that he was certainly struggling on a certain level. It was hard to say what level, but there were delays and work stops.

Wallach: The next thing I knew, I got a call on a Friday in April from Michelle [Armour], the producer. She was like, “We don’t know where Dave is.” “What do you mean, ‘You don’t know where Dave is’? Did you call his wife? Did you call this place? Did you call that place?” “Yeah. We don’t know where Dave is.” I was like, “Do I need to call the emergency rooms at hospitals?” It was awful.

Fox: Dave’s departure was probably number two in terms of PR crisis in all my years there. I kept begging his agents and managers, “Tell me what happened! Tell me where he is! We’ve got to put a stop to this!” The media was just speculating wildly in absence of facts. It was the kind of story that just wouldn’t go away. But his agents, his management, they didn’t know where he was. His wife didn’t know where he was. It was a very, very difficult time.

Herzog: One morning I woke up and somebody said, “Dave’s gone. He went to Africa. And no one knows when he’s coming back.”

Wallach: It was revealed that he left. He “had to get away.” He went to South Africa. By that point we had been bought out by Viacom, and it went up the corporate food chain very quickly on how to handle this. In hindsight, I think everybody had the right intentions of how it was handled. I feel like they sort of pushed aside folks like myself and one or two others who could have been more helpful to the process in terms of communicating. But they would just call me and a couple other people in and be like, “Well what happened here, here, and here?” You gave them the information, and then you really didn’t know what the next part of the conversation was.

Rawlings: At the time we were shooting Chappelle’s Show, I created the “I’m Rich, Bitch!” tour. We were making some money, but we definitely weren’t making huge money. But we were popular. People knew who we were. I put together myself, Bill Burr, Charlie Murphy, and we started the “I’m Rich, Bitch!” tour. So when Dave left, it really gave us the opportunity to go out and make some money. I didn’t think it was going to be final. When Dave said he was going home, I thought he was going to Washington, D.C. I didn’t think that he had the idea of going home home back to Africa. I didn’t know if that was a good time to make a pilgrimage to find out what your roots were. But come to find out, the show was over.

Fox: I had a decision to make when the Oprah Winfrey Show called. They wanted to do a piece with Dave, and we knew exactly the danger of him doing that and sort of painting the network as the bad guy. But we cooperated. It was a decision I made. I thought it was important, and I thought Oprah and the show would appreciate the fact that we gave the material to them in the hopes that they would tell a fair and balanced story, and I think they largely did. Dave, even explaining himself on the show, you realize that something was up.

Rawlings: That’s the question no one has the answer to. The only one who has the answer to that is Dave.

Fox: I can’t really explain what happened. There are a bunch of theories about what actually happened. I’m not sure which one is true.

Herzog: When you think about somebody walking away from the game at the top of their game, it doesn’t happen very often. I don’t know if any of us were quite prepared to deal with it.

Fox: We knew Dave had issues that he had to deal with. Ultimately the network decided we were willing to wait for him because of his brilliance and our relationship with him, and our belief in him. We basically said to him, “Listen, when you’re ready, come back. The door’s open. We’ll put production on hold.” We had shot material for season three. Much of it was great, and we wanted him to finish it. We basically said, “The door’s open,” but unfortunately he never came back.

Blender, April 2004

Ganeless: I came back as season three production was starting, and honestly just got through the tail end of Dave’s exit. The challenge then was “What do you next?” You can’t really replace a show like that, and you have to just look for the next viewpoint.

Wallach: The network had huge plans to launch other things off of it, and I think the network made some programming decisions very quickly to creatively try and imitate that. Look, you can’t imitate that. It’s inimitable. It’s the reason you want that show, or any other show: It’s because they’re unique, they’re specific, it’s an un-watered-down point of view. You don’t just walk down the street to the Chappelle Replacement Store and pick up a handful.

Rawlings: People asked, “Was I upset?” I was upset because I didn’t have the opportunity to work with a tight cast and good friends [any longer]. But it just felt weird because we were still at the height of it, and there was so much love on the streets. I just really was excited about giving people what we had been delivering for the last two and a half years. So that was the unfortunate thing about it. On the other side of it, the show gave me a platform for people to see what I could bring to the industry in terms of talent.

Herzog: It certainly ended badly in that we went ahead and tried to make some episodes with Neal Brennan out of what he’d left behind, which left him very unhappy. That was the last time we talked until I went to see him two years ago on the Oddball Tour. I said hello, and he couldn’t have been nicer, as he always is.

Esquire, May 2006

Fox: We had nothing but sympathy for him, and I still to this day miss the guy. I miss him performing, I miss his humor, I miss his sweet nature.

Wallach: I think he could have continued to do great things. I don’t know what went on in his head. But it was a shame, because I think he put a lot of great people who were really, really devoted to the show on the production side out of work. I’ve never talked to Dave about this. We have a good, cordial relationship now when I see him, which isn’t often. He gave me a big hug when I saw him in Montreal this past year and said, “Hey man, we did something really great back then, didn’t we?” I said, “Absolutely.”

Wilmore: It was so funny, and it’s still funny, which is great about Chappelle’s Show. You can still watch it and laugh.

Herzog: Dave came to our Justin Bieber roast, and I ended up having a really lovely conversation with him at the afterparty. He hung out for a while and, you know what, Dave’s doing great. He’s in great spirits, and he’s one of the greatest at what he does. He’s a genius in his own right. I’m not sure any of us understand, maybe including him, what happened way back when. I think it was meant to be, on a certain level. You look back at those two seasons, and they’re two of the greatest, funniest seasons of sketch comedy anyone’s going to do, ever. And it was kind of like “drop the mic” time.

2003: Reno 911!

“There was never ‘no’ on set, and we made that really clear.”

The cast of Reno 911! (photo: Comedy Central)

As President of MTV Productions, Doug Herzog oversaw 11 young sketch subversives through four groundbreaking seasons of The State. In 1995 the group departed for an ill-fated test special at CBS; that same year Herzog was named president of Comedy Central.

By 1997, The State producer Jim Sharp had similarly relocated to Comedy Central as vice president of development, and Thomas Lennon, Ben Garant, Kerri Kenney-Silver, and Michael Ian Black were a go for a satirical State spin-off promising mangled sponsor plugs, absurdist game shows, and carte blanche for the hair and wardrobe departments.

“I believe we were all were musical-theater nerds at heart, and we got to go to Vegas and dance with the Rockettes, sing with Nell Carter, dance around with Stacy Keach, all kinds of stuff with Whoopi Goldberg and Shelley Long,” Kenney-Silver reminisces. “We had insane musical guests like Run-D.M.C. It was the most fun I’ve ever had.”

When Viva Variety ended in 1999, Lennon, Garant, and Kenney-Silver had relocated from New York City to Los Angeles, and were eager to begin a new sketch project at Fox. A few false starts and one network switch would eventually birth a new mode of televised improv, a feature film, and one of longest-running shows on Comedy Central.

Herzog: I ran the Fox network for about a minute and a half in 1999. I think I sent the land speed record for network president. But in my short time there I commissioned a pilot from Ben [Garant], Tom [Lennon], and Kerri [Kenney-Silver]… which was a failed pilot.

Kerri Kenney-Silver: Tom and Ben and I had a deal with Fox to do a sketch pilot before Reno. We hired a cast of sketch actors—no improv at all—and we wrote a tight script like we used to do for The State.

Herzog: They had been working together so long, they had an almost telepathic comedic relationship with each other. That kind of chemistry doesn’t happen overnight. Then they went out and found some like-minded and very talented people to flesh out the rest of the cast.

Carlos Alazraqui: I was in the original Fox pilot audition with Ben and Tom and Kerri, who I had not met before. I had never seen The State. So I didn’t know them, which I actually think in the long run helped because I would have been way too intimidated. I did my audition with multiple sketch characters and got all the way to the table read with [subsequent Fox President] Gail Berman.

Kenney-Silver: All through the process we kept saying, “All these networks are saying they want to do sketch again, but then when we get into the process, they get nervous.” And sure enough, at our table read, it’s silence. There is no laughter from the executives. We left that table read going, “Well, that’s not going to happen.”

Herzog: I had then left Fox, but the Fox development team kind of fell in love with them and commissioned another pilot, which turned out to be Reno 911!

Kenney-Silver: That night we called each other and talked, and said, “Hey, we have no money left. It’s all been spent on this sketch show that’s not going to happen. What if we did a spoof of Cops, which is on their network? It relates to the network, and what the hell—we have nothing to lose. But we don’t have time to write a script…” We pitched it to them, and they said, “Sure, why not?” And now this cast that we hired—Niecy Nash and Cedric Yarbrough and everybody—all the sudden we called them and go, “Guys, new plan. Do you know how to do improv?” Everybody was like, “Great, let’s go for it.”

Alazraqui: After that they said, “We’re gonna do something called Reno 911!, and make fun of Cops. So you just go home and think about some characters.” I’d always been drawn to those asshole-prick characters, self-righteous, a little bit of Barney Fife, a by-the-rules guy. I was the older person in the cast, so I thought that would fit right into my own natural age difference. I thought about my college roommate, a guy named Dan Garcia. He listened to country music and married an Irish woman, always very mellow and upstanding. I thought, “That would be a fun name for a self-loathing, or not-accepting-of-his-own culture guy. James Garcia, let’s play with that.”

Kenney-Silver: It was just a matter of renting cop uniforms and going into back alleys. So we just picked names, had name tags made up, and made that pilot.

Alazraqui: Beth McCarthy-Miller was our director. She had come off Saturday Night Live, and Ben and Tom and Kerri had written up all these scenarios. The first one we did was the mime thing. We were inside this empty studio warehouse at Sunset and Bronson. Ben gets up as a mime, and we just started saying a couple of things. It was about a two-minute rehearsal, and then the rest just took off. When Fox passed on the pilot, we were disappointed because we knew it was funny.

Kenney-Silver: Fox said, “We love it. It’s great. We’re not going to pick it up.” So it sat on the shelf. And then five years later Jim Sharp said, “Hey guys, remember that pilot you did for Fox? Let’s take a look at it.”

Alazraqui: He liked it, and then we heard we were going to series sometime around 2003.

Kenney-Silver: We thought Fox would never sell the pilot. Usually when a pilot gets made by a network and they don’t pick it up, they don’t release it to someone else later, because what if it’s a hit and they let it slip through their fingers? But they did let Comedy Central buy it, and we were off and running with the show.

Alazraqui: One of the most brilliant things they did was on the first day of shooting, they had 20 questions for each of our characters. It helped define our characters and also our relationships with other characters. The characters were strong, and it wasn’t just about the calls. It wasn’t just about the guy on the roof or the stripper on the bed. It was about the inter-relationships.

Kenney-Silver: As actors we could more easily put ourselves in the shoes of the person coming in to audition than being the producer on the other side of the table hiring cast—because we knew how they felt. It was scary enough auditioning people for this supposed sketch show pilot that we were doing on Fox, but that was an animal that we knew: written sketch. But to ask somebody else to come in and improvise on an audition, when we saw ourselves as improvisers, was terrifying. But it turned out to be one of the best parts of doing Reno.

Alazraqui: What I liked about the first couple seasons was it was totally hands-off. Jim Sharp was there, but he was like one of the guys. Occasionally we’d have some producers, but it wasn’t like these overwrought table reads and pink pages and blue pages and jokes after jokes after jokes and beating it to death. It was the opposite of a three-camera shoot. It was like, “Yeah, this seems funny. Go for it!” We would line up the scene, and [director] Michael Patrick Jann and Tom and Ben and Kerri would watch it, and go, “Oh, that was good! Only this time try to get to this point quicker!” or “Oh, that was a good one too! Let’s just do it one more time and see what happens!” or “Good! Got it! Moving on!” There were no executives to spoil it. They just let us be us, and it worked. We started to gain confidence in our characters.

Kenney-Silver: For the people we called in, the casting person, Julie Ashton, would say, “Okay, this is basically a spoof of a cop show. We want you to go in the room and tell Tom, Ben, and Kerri that you are either calling the cops, or you’re getting the cops called on you. And then one of the—or all of them—will get up and improvise with you.” It was so fun and so humbling, because there’s immense talent that comes out of UCB and IO West and all these incredible places in Los Angeles.

Peele: The episode I was in was when [UCB co-founder] Ian Roberts—who coincidentally ended up being one of Key & Peele’s showrunners—was there. That was the first time I ever sat down and had a good conversation with him after knowing of him for years in the improv community. But the thing I most remember is that the cast and writers and team over there were such cool people, and had such a great process that was a blend of written material and improv. I’d done that before, but the way they did it was pretty evolved.

Natasha Leggero (Another Period): Reno 911! was pretty much how I got my start in comedy. I had this manager, Bruce Smith, who was like, “I’ve gotta get you in front of these people!” You’d go to the audition with Tom Lennon and Kerri Kenney, and all you had to was improvise with them. They’d say, “So are you being arrested, or did you call the police on someone?” That’s all they wanted to know for the audition. I had this idea that I would play this girl that couldn’t find her pants. I came into the audition in, like, a big football jersey with no pants on—I think I had on short shorts or something underneath—and I was like, “Someone has called the police on me.” Then we just did this crazy improv, and it was so funny. Two months later I was cast as “Pantsless Hooker.”

I learned so much improvising with them, because as a comedian in an improv situation, your instinct is often just to say “no.” But improvisers, they say “yes” to everything. I remember at one point I was being arrested by Tom Lennon, and then I asked him for a cigarette. He was like, “Oh yeah, of course,” and he starts fumbling through his pockets trying to get me a cigarette, and I was able to run away. That instinct to say yes really creates these comedic moments. Your rational brain is like, “No, you can’t have a cigarette. I’m arresting you.” But if you really do go by the rules of saying yes, amazing things happen.

Kenney-Silver: There was never “no” on set, and we made that really clear. I think the fact that we were there to play with them put us in a unique position of understanding that when you’re an actor who’s improvising, you just want to say “yes” and have “yes” said back to you so you can move forward in a scene. We knew that the sky had to be the limit.

Key: Their auditioning was so interactive. I used to audition people in the same way that Ben and Tom and Kerri auditioned me, which was that one of them would be onstage working with you. And I love the fact that all they wanted was the loose scenario. All they wanted was for you to have fun. To me, that’s how all auditions should be done. They should try to make the artist as comfortable as possible so they can put their best foot forward without an ounce or iota of fear surrounding the process.

Kenney-Silver: Keegan-Michael Key stood out in all of our memories, and I think would be in anyone’s top three of greatest guests we ever had. We laughed so hard every time we were together.

Key: I remember them putting their money where their mouth was when we got to the production process. On that show it was as much of a delight for the performer to perform with the leads in the show as it was for the editor to put the stuff together. Because it was truly an improvised show. I kept on thinking, “God, I hope later in my career I have an opportunity to work on a show like that, where you get to take a scenario and just go off with it.” It was really terrific.

Alazraqui: I had thought of this scene where we see this guy coming out of a casino with a wheelbarrow full of chips. The gist was we were just going to let him dig his own hole: “Okay, what happened was, like, the machine just started going crazy and the lights went out and everybody ran, and I thought, ‘I’m gonna collect all these chips and then make sure that they get protected, so I’m taking them back to my house.’” Cedric and I’s instinct was just to let him go, and say nothing while we ate our peanut butter-jelly sandwiches and drank our soft drinks. And then we just weren’t jelling on that scene together, so they wanted us to interact with him. Either way the scene was great, because Keegan-Michael Key was brilliant enough to drive the scene, which didn’t require a lot of work from us.

Key: There was one episode where I was running down the street wearing sweat pants and tuxedo shoes, and Cedric Yarbrough was in pursuit. I thought I was gonna eat it about six times. There was no tread on the tuxedo shoes. I was like, “This is would be a great workman’s comp story: ‘How did you chip your tooth, sir?’ ‘Well, I was wearing a costume with cow udders and running down the street in tuxedo shoes…’”

Kenney-Silver: For maybe half the people that we liked, we would find something for them to do, maybe play a stripper in a scene we needed to cast. And then the other half would come in with a finished product. For example, Nick Swardson—who is an old friend of mine I knew as a kid—he came in, like, “What if I’m wearing roller skates and I am a hooker on crack?” “Done! What do you need us to get you? Roller skates and Twizzlers? Great, we’ll see you on Tuesday!”

Lisa Lampanelli: They had me come in as this lesbian priest doing a gay wedding, and we had a blast. We improv-ed a lot of scenes that didn’t make it in; I would love to see the outtakes. But that was an experience. What a bunch of pros. Because when you do improv with real pros, you think you suck, like, “Oh, I could never!” But I think that gave me a lot of more confidence to go, “Oh, I can do this.”

Alazraqui: I was remembering the other night the Halloween egg fight in the cemetery, where I really just liked the stupid line, “We’re gonna count to 10, and my partner will count.” Also being in the car with Kenny Rogers. [Producer/Sniffy The Drug Hound actor] David Lincoln had given me a bunch of the Brady Hawkes movies that I just went to town on and took a bunch of notes. Kenny Rogers was right there; he did not miss a beat.

Kenney-Silver: We had an unbelievable crew of people who were committed, enthusiastic, and invested emotionally in the show. Everyone was on their toes. No one was sitting back, picking their nose, waiting for the next scene. If an actor in a scene—a guest or any one of us—all of the sudden said, “I’m going to go grab a Slurpee,” then the prop department was scrambling with a cup so that we have that Slurpee when someone steps off. Or that the cars are running, so if a perpetrator wants to jump into a car, it’s there and ready, and they can take off. The guns were of a real weight so you could pull it out of a holster and act with it.

Alazraqui: There are so many favorite scenes to chose from: I loved all the stuff with Cedric, because we had such good chemistry. Me spooning Tom Lennon in the cop car, and the firemen sawing open the roof to find us together. The big kiss I planted on Dave Holmes when we arrest [Debbie] Dangle’s boyfriend and I try to pretend that I was always in love with him—again, that was one they didn’t know was going to happen. The anniversary where I went crazy and shot the piñata: “You motherfucker!” Again, they didn’t know I was going to go that far. The looks on their faces was kind of real, like, “Oh, Garcia’s not crazy. Carlos is crazy.” That was the show in general: You didn’t know what anyone was going to do or say, and it really made for great moments that are indelible and unforgettable, and that I’m still trying to create in things that I shoot or pitch.

Kenney-Silver: There really were very few boundaries, and we felt that was important. That was what we wanted, and of course anyone that came to play, it was encouraged. It was like, “This is your space. And if you want to do it again and have us tackle you, or have us let you get by, just let us know.” Because it was all for the good of the show, and I think that shows on screen. You get the sense that anything can happen, because it did.

Alazraqui: It was not over-written. It was obviously all improv. And it was very irreverent and stupid and silly, and it harkened back to good ol’ slapstick days. It wasn’t trying too hard to be cool. Especially in that way we dressed, for God’s sake, in that gross beige color. It wasn’t pretentious. I think that’s why people liked it. It caught them off guard.

Key: It was really always a fun time being on that show, and just the conceit of it was fantastic. Reno was a real lynchpin for that network.

Colin Quinn: Every cop I’ve ever talked to has said the most realistic cop show they ever saw was Reno 911!.

Fox: We always looked at our programming as a portfolio of shows, and to have something like that in your schedule, it was just invaluable. Something Comedy Central was trying to do was to nurture long-term relationships with creative talents with very distinct points of view, and I think the Reno guys clearly were that. And they were a gas to work with.

Herzog: It was the right show at the right time in terms of doing a parody of something that was very present on the television landscape at the time. It is one of the great Comedy Central shows. And later a motion picture.

Kenney-Silver: Once we found quite a bit of success with it, our lawyer called us one day and said, “Hey, I was just looking through the contract. You’re not going to believe this, but Comedy Central failed to buy the movie rights from Fox. So Fox owns the movie rights, and Fox would like to make this as a movie.” So we did the feature with Fox, in conjunction with Comedy Central. But it was Fox’s film. So that was a pretty remarkable experience for us to be able to do both the show and a film with those same characters in that same world.

Alazraqui: It had to be a little more plot-intensive, and also a little more plotted-out. It wasn’t exactly the freedom we had on the show. There was still some improv, but it had to sit within the context of reaching a broader audience who had never seen the show before. With our audience, we were allowed to be subtle. The half-hour episodes could be repeated and watched a couple times. Not so with an hour-and-40-minute film. Plus it had to be more cinematic. I couldn’t have a fake mustache, for example, because it looked bad in HD, so we had to grow our own. And it was a challenge to try to concentrate when you were in South Beach, Miami, getting a per diem every day and getting to party every night.

Kenney-Silver: It was a challenge sustaining the story long enough, because things were moving more toward a quicker, faster way of digesting comedy. So it really had to be fast-paced. Changing something from 22 minutes to a whole film was a challenge. But by that point, we had great guests calling us, saying, “Can we be part of it?” The thing most people who aren’t mega-celebrities have a challenge with when they’re doing a feature on a lower budget is getting great talent in, getting names and stunt casting and stuff. And we had that already built in. One call to Paul Reubens, and he was like, “Oh my God, absolutely! When do I come? What are we doing?”

Fox: After seven years clearly the show had started to deteriorate in terms of its performance, and we had made a movie, and I think the DVD sales at that point had kind of leveled off.

Ganeless: Both Tom and Ben were starting to write movies. They all had so many different things they wanted to do. And it had sort of run its course. It was a lot of content they had created over so many seasons.

Fox: A lot of these guys were starting to become successful and getting offered other opportunities elsewhere. I do remember the ending of the show being a little rough. It was a tremendous run, but there was a little bit of friction when the network and the show parted ways. And I think ultimately the programming folks regretted that, because those are the kind of people you want to be in business with forever if you can do it.

Lampanelli: Those guys were the best, and that was one of the best shows on Comedy Central. I loved it, and miss it.

Kenney-Silver: In hindsight, I feel really good that at the time, that wasn’t happening in the world for improv actors. That was the only outlet. The only other show that I’m aware of that was doing improv—Curb Your Enthusiasm—that’s not how the audition process worked. You’d come in to audition for a specific a part that was written, and you’d improvise with Larry or someone there. But on our show, you could come in with a character you’d been working on or an idea you had, and get to flesh it out, have us say, “Sounds great!” and then come and play it out on TV. Later we heard from other actors, “God, that was the most fun I ever had! Where else do you get to do that?” Now it’s become a model, and now there are endless web series and TV shows and films. I’m not saying we invented this style of working, but certainly on television we were the only game in town for a while that offered that opportunity. And I feel good about that.

2005: The Colbert Report

The big question was, ‘Can this character, can this conceit, last longer than two weeks of test shows?’”

Stephen Colbert interviews Barack Obama for a 2014 episode of The Colbert Report (Photo: Getty Images)

Fox: We were the comedic political voice for many, many years. And Stewart/Colbert was the ticket. People were making Stewart/Colbert bumper stickers in 2004! It’s insane the popularity that these guys had, and that was one of our big strategic pushes early on: To be that voice. I don’t know that we’ll have it quite to the extent that we did since the Stewart/Colbert years, but that was an extraordinary position to be in: the preeminent political satirists in the culture. I think it is an important, extraordinary accomplishment.

Wallach: Stephen Colbert has been really good for a really long time, in Strangers With Candy, back in some of the Second City stuff online, when he was writing for The Dana Carvey Show. Even when you just have a conversation with the real Stephen Colbert, it’s not a show. He’s a family guy, an approachable guy, a Sunday school teacher. He has figured out how to have this real work-life balance, where I think one has to inform the other.

Fox: We were always looking for a companion show to follow The Daily Show, because it would deliver this great audience to the network at 11:30, and then everybody would disappear. So it became almost an imperative to find something that would be seen as a companion piece and carry the viewers right through to midnight, or to 12:30.

Ganeless: When I got back from USA, Tough Crowd was ending. I wouldn’t say we were specifically looking for companion programming, but Stephen had such a fully formed vision for The Colbert Report. If I remember correctly, while we were at the time also sort of flirting with some other late night ideas by D.L. Hughley and Adam Carolla—who are both brilliant in their own right—Stephen’s show was just so perfectly suited as a companion and as a stand-alone, brilliant piece of comedy.

Fox: Obviously his character on The Daily Show was well established. I think it was in 2004 at the Democratic Convention coverage that we did up in Boston, Stewart and Colbert were doing this bit about Colbert’s great-grandfather being a turd farmer or something. It was the most ridiculous bit ever, and they couldn’t get through it. They were just howling laughing as Colbert’s playing this character, and Jon just could not keep it together. It probably took an hour to shoot the thing because they could just not get through it, they were just laughing so hard. So it became clear long before The Colbert Report launched that Stephen Colbert the character had a potential life of its own.

Wallach: He truly is one of the most brilliant, well-rounded performers-artists in everything: actor, writer, director, improviser. The guy sings. The guy dances. And he is hilarious. It was a no-brainer.

Fox: Jon’s production company existed because he was the executive producer of The Daily Show itself. This became the next show that was produced out of Busboy Productions.

Wallach: Jon Stewart was definitely involved. This was a character Stephen was honing for years in shorter form on The Daily Show. Some of the producers like Ben Karlin came over, and some other people from The Daily Show were involved in the development of it. It was a Busboy Production, but Allison Silverman and Rich Dahm came on, two of the smartest writing producers I know. There were a lot of smart people in that room. I think the smartest thing we did was not get in the way and “out-smart” them. Our job was to ask the right questions as a sounding board—and we didn’t even have to do that. The big question was, “Can this character, can this conceit, last longer than two weeks of test shows? Is this a sketch? Is this a gag?”

Ganeless: It came out of the box fully formed, episode one. Which is—especially as we watch all the other late-night shows evolve today—incredible and extraordinary. He had a very specific idea of what he wanted to do with the character he had evolved on The Daily Show.

Fox: The show debuted with Stone Phillips on, and “truthiness” was immediately coined and became the “word of the year.” But everybody was predicting a short life for the show, because they just didn’t believe that someone could sustain a character in a live talk-show environment like that. We did it with Jiminy Glick, but that was weekly for three seasons. No one thought Colbert could pull this off for the period of time that he did. And not only did he do it, he did it brilliantly.

Dan Powell (The Daily Show, Colbert Report, Inside Amy Schumer): When I was assigned coverage of Colbert Report, it was already a couple seasons in. A lot of what I did was facilitating the communication between the producers of the show and the ad sales executives at Comedy Central. I got a very grandiose title for what was essentially a figurehead position. My job was really being the sort of gateway between the network and the show.

The show actually did a lot of groundbreaking, experimental stuff with integrated content, like how Doritos sponsored Colbert’s presidential campaign. They really did a lot of inventive things with the ad sales department, figuring out a fun, creative way to get sponsored, integrated advertising into the body of the show itself in a way where Stephen could acknowledge it and be self-deprecating about it. But also it brought some money into the network and to the show.

Fox: The freedom that that fictitious character gave him to do things that Jon couldn’t do just made the show. It takes a special, warped kind of person to really appreciate Colbert and his whacked-out gourd. But every time he got involved in a poll, naming a bridge, I couldn’t believe Colbert Nation and the way they were reacting. It just blew my mind. It was a phenomenon, and quickly became irreplaceable in some ways pertaining to The Daily Show.

Wallach: I never thought I would live to go to a White House Correspondents’ Dinner, and I got to go to that famous one. It was amazing. It was as awkward in the moment as the Chevy Chase Roast, if not worse, because the president of the United States is standing 20 feet from me. But in hindsight, it was genius. My guess is at a certain point he was like, “Oh, what did I just do?” But he committed to it. That’s that Chicago Second City training. He committed to it, did it, and it was brilliant.

Herzog: Colbert took The Daily Show impact and turned it into what I used to call “The Daily Show Network,” which was an hour night versus just a half-hour night. It was an amazing, one-of-a-kind offshoot; one of the great spin-offs in the history of television. It was a genius, virtuoso comedic performance every night for nine years that will never be duplicated.

Fox: The only unfortunate part of that kind of success is sometimes your talent that you invest so much time and money in grows bigger than you. They move on to movie careers and other great things, which again, you’re always proud of, but you hate to lose a guy like Colbert or a guy like Stewart, or anyone else.

Alterman: Of course we want our talent to blow up; that’s the whole name of the game. But we also don’t want to put shackles on them. I think there’s a lot written about talent that has left the network, but if you break it down, we got 16 years from Jon Stewart. He earned his right to take a break. Stephen Colbert was with the network in various forms, from his original sketch show to being a correspondent on The Daily Show to being one of the creators and stars of Strangers With Candy to having his own show. He spent around 20 years on the network. So it’s easy to say, “He’s jumped ship!” but that’s a long time to have someone. In Stephen’s case, he was doing a character, and the question was always “How long is he going to want to be doing that character?” I think at a certain point he had just done it enough.

2011: Workaholics / 2013: Adam DeVine’s House Party

“Camera over there and there, and Adam will sit here. But be quiet, because Adam’s still sleeping in the next room.”

Anders Holm (left), Blake Anderson, Adam DeVine (photo: Comedy Central)

Mail Order Comedy formed in Los Angeles in 2006. Within two years their unapologetically low-budget YouTube sketches landed Blake Anderson, Adam DeVine, Anders Holm, and director Kyle Newacheck both a hidden-camera and an action-spoof series for MySpace. A rap video about immortality-boasting wizards quickly spawned 2009’s high-concept, character-driven album Purple Magic.

The DIY efforts generated more views than sustainable income. But the Funny Or Die web miniseries 5th Year soon inspired a Comedy Central workplace sitcom about a group of dropout/burnouts navigating young adulthood. As later recalled on Conan, Mail Order Comedy was so sure the pick-up was a fluke (and was also so broke), cast members lived for the first season in the rat-infested Van Nuys four-bedroom where home scenes of Workaholics were shot. They would eventually comprise one of the longest-running and most-loved ensembles in Comedy Central history.

DeVine: We were working really hard, taking our sketch comedy so seriously. We were coming out with 80 videos in two years: producing, writing, and acting in them, scrounging together whatever costumes on whatever budget we could afford.

Kyle Newacheck: We were internet guys that did YouTube. We made a webseries and put it on Funny Or Die. That sat dormant for about six or seven months until a development executive named Walter Newman saw it, called us up, and said he liked it.

DeVine: I had done Live At Gotham in 2008. That sort of put us on their radar, and they watched some of our stuff. Our manager submitted a CD-ROM of our material. Walter Newman, who’s now over at Adult Swim, and Seth Cohen, who’s running the Lego guys’ Lord Miller [Production Company], they were the ones who found us in a big stack and thought we had a voice.

Fox: For us it was a great example of finding brilliant talent on the internet. And like much of Comedy Central talent, these are people who write, produce, perform, they do it all themselves, like the Reno 911! guys, like the South Park guys. It’s just a great way to work, and that’s what these guys were.

Ganeless: I remember watching the pilot and thinking these guys were so authentic, and the chemistry between them is one of those things you cannot create. Certainly you can cast a show like Friends and find actors that can create that chemistry, but these guys had it because they live it. That’s such a key element to a Comedy Central show: a unique vision. Whether it’s one person like Dave Chappelle or two people like Matt [Stone] and Trey [Parker] or the four Workaholics guys, it was their one unique vision. The show just felt so of-the-moment for that generation, who still talk about it even as they age and are leaving college and actually becoming adults. That pilot jumped off the page, for sure.

Fox: Very often you wonder if talent has the ability to grind out scripts that can carry a story, and carry a story for a long period of time. These guys were already doing it in these webisodes. Programming is such a hit-or-miss business that when you have somebody that already has a track record of success and already has a bit of a following as well, obviously it’s a little easier to market a show that has an awareness.

DeVine: The mandate was, “Let these guys do what they do. We think they’re funny; let them be funny.” I think it also helps that they didn’t have a real stake in our show. They weren’t paying us a fortune. None of us were stars: “If it works, great. If it doesn’t, on to the next one.” So they left us to our own devices. It was awesome having that freedom, but at the same time it was really scary. We’d ever written a TV show before. I was literally reading a book about how to write for television while I was writing my own television show. I had to learn fast.”

Newacheck: In the first year of casting, we wrote this character for a tech-savvy, hip-hop-talking dude. Erik Griffin rolled in, and he just was Montez. He has been nothing but a great asset to the cast. And Jillian Bell, we knew her from before Workaholics, in our sketch days. We met her doing work with National Lampoon. She was always a star, and we had a role for her. Maribeth Monroe, I think, was Chicago Second City. Ders had seen her maybe five years before we cast her. In the audition she had to rip Adam a new asshole. It was like, “Yeah, you’ve got this. This is the dynamic we need.”

DeVine: Something else Comedy Central did that not a lot of other networks would have done is cast all three of us, and Kyle as our director. I feel like another network could have easily gone, “We don’t like Adam’s look,” or whatever it is. They could have cast someone else or said, “We needed a more experienced director at the helm.” But they let us do what we do and gave us the opportunity to work with our very best friends.

Newacheck: If we had a call time at 6:30, I’d wake up in the house at, like, 6:15, go put a pot of coffee on, and unlock the door for the trucks filled with grown dads waiting to come in and start lighting the scene. I would tell the crew what we needed to do with the scene: “Camera over there and there, and Adam will sit here. But be quiet, because Adam’s still sleeping in the next room.” I would take the sides and just slip them under his door.

Erik Griffin: Workaholics sets itself apart because of the chemistry of the three boys. I think they’re like the modern-day Three Stooges, and it’s very relatable to a certain age group. The people who watch really feel connected to the show. People always stop me in the street and I hear things like, “Oh, that’s me and my friends!” and “Oh, we love to smoke weed and watch Workaholics!” It’s just relatable to a certain age group, and there’s been nothing like it on TV. It really is a testament to the boys’ hard work that they put into it.

DeVine: We didn’t realize the show was a hit until after season one had come out and we were working on season two. We went and did Bonnaroo that year. In L.A. people will tell you they love the show, but it could just be a producer or agent trying to sign me. You just don’t know. Especially if they’re wearing cool sunglasses and jeans with bedazzled pockets. So it was cool to get out of town, go to rural Tennessee, and just have all these fans. Security told us, “Hey, it’s not safe for you guys to go out there. We have to take you on the back roads.” We felt like rock stars. It was the first time we felt, “Wow, people actually watch the show—and like it!” It was a pretty incredible feeling after working so hard for years and getting moderate success, but nothing on that level.

Newacheck: We went to Australia to help promote Comedy Central. When Ders and I were walking down the street, people were like, “Ders!” I said, “We are on the other side of the globe right now, and somebody just yelled your real name.” It was a trip.

DeVine: If you told 16-year-old Adam that through a wealth of dick jokes I’d get to hang out with NBA stars and rock stars, I’d have been pretty astounded. I would have had something to promise my parents when I told them, “I’m not going to school! I’m doing comedy full-time! Believe me, it’ll work out!”

Newacheck: I was raised in a Christian family, so my mom thought Trey Parker and Matt Stone were the devil. I was not allowed to watch South Park at the house. Cut to 10 years later, when my show is premiering after South Park. I’m pretty sure Workaholics was just a product of teenage rebellion against my parents.

DeVine: I’ve gotten to meet my heroes, had Blake Griffin tweet at me and invite me to games and become friendly with him, and had the Black Keys become good friends of mine. We got them on an episode of Workaholics in a little cameo.

Blake Griffin: Adam and I go to Clipper games together. I go to dinner and lunch with Jillian and Maribeth [Monroe]. It’s a pretty tight-knit group. We’ve gotten pretty close over the years.

DeVine: We’re coming up on our seventh season, which I think ties Reno 911! as the longest scripted series in Comedy Central history. We’re all at the point where we’re wondering if we’re too old to be sitting on the roof, smoking blunts, and chugging beers with each other. The answer is no, but I think we’re all getting excited and ready to go and try other things.

Newacheck: We are going to sit down and start cracking season seven next week. Then that’s going to be it for us. We’re going to go out with seven, I think. Eighty-six episodes is a lot. So now we’re going to try to make movies and stuff. But lord knows what we’re going to do with season seven. I don’t know how, but we’re going to get it all out.

Alterman: They’ve been amazing. Like many of our most successful shows, they are the creator, writer, producer, and performer of their material. They are just embarking on their seventh season, and who would have hoped for or expected that? We’re really grateful for their success. As far as seeing them evolve, they just keep getting better at what they’re doing, and because of that their opportunities keep expanding: They are now directing as well. They just have such a strong sense of who they are and what makes them authentically funny.

Fox: Workaholics was a brilliant, brilliant find and so consistently funny. They’re another example of what Comedy Central always aspired to be, a home for people that had really smart, funny ideas. We wanted always to support people and grow them in their careers, and already some of these guys are developing movie careers.

Newacheck: Before there was Workaholics, I used to go watch Adam do open mics back in 2004. I had graduated from film school, then we were living together, and he was just doing the open-mic circuit all over Hollywood. I’ve always been a fan of his stand-up, and I just really enjoyed the craft. We were talking about doing a stand-up special that would take stand-up outside of the conventional stage.

Larsen: Adam DeVine’s House Party was an idea we’d been toying with—not that specific concept—but the idea of creating a show for young talent where they can do a five-to-seven-minute stand-up set, but also potentially showcase some of their acting abilities or their abilities to do sketch. A lot of the comics obviously have aspirations in a multitude of directions. Some of them end up focusing on stand-up, and others do more acting in comedic roles, or writing. So we wanted to create or put on a show that could highlight some of those. I was talking to David Martin at Avalon, and I sort of expressed that desire. He’s like, “You know, I think Adam has an idea you should hear.”

DeVine: That was an idea I’ve had since high school. Watching all the old Comedy Central Presents, they’d point the camera at a comic backstage, and they’d make funny faces or do a dumb bit. Then they’d go onstage, which was decorated in relation to their set, and I just thought it was so cool getting to know a personality through their stand-up. Live At Gotham was off the air, and there wasn’t a “new faces” stand-up show, so I went to Comedy Central and pitched them the idea.

Alterman: We always try to have some mix of stand-up vehicles to not only fill our content pipeline, but also fill our development pipeline. A show like Adam DeVine’s House Party is a great vehicle for introducing new, emerging talent on another level. As people continue to grow, that’s another vehicle for us—both program content, and also just to continue a relationship with people. Many of those people are the ones that do hour specials later, or their own shows. People like Amy Schumer or Daniel Tosh and so on, they’ve come through that pipeline. We always like to have a mix of people at different levels, and Adam DeVine’s House Party has been a good one for more emerging talent.

Liza Treyger (Like It With Liza): You get to be in the sketches with him. He’s so talented, and it was exciting to watch him work. It was my first time on a set with a little trailer. Being able to be in a scene and do stand-up was really exciting.

DeVine: Stand-ups aren’t necessarily just stand-ups anymore. They can write and act and produce, and it’s fun to write a little story and get to see some of their personality, and for Comedy Central to see some of their acting chops.

Treyger: There are no language restrictions, you don’t have to be clean, you don’t have to stick to anything, and I just like that full freedom. Adam called all the comics and had a chat where he was just like, “Be yourself, have fun, go long if you have to. I don’t care. Just enjoy yourself.” That’s the most freeing and exhilarating thing to have no notes, and you know you can take a risk or add something because they’re going to edit it down anyway. It’s just magic to be told to do what you’re about, and not have to switch for any reason.

Ganeless: What I think Adam is trying to do that hasn’t been done before is break the format a little bit. It’s not just a brick wall. There’s sketch, and it’s just really fun. It’s not surprising, because that was always the intent.

Newacheck: Season one was an experiment. We put the stand-up in the back yard. Then we took the stand-up and brought it to New Orleans, and explored their musical culture along with the stand-up culture. Then we took it to Hawaii.

DeVine: I’ve gotten to do House Party for three seasons now. I thought I had it as good as I could when we went to New Orleans. Then I shot a movie in Hawaii this summer and said, “Oh, it would be amazing to do House Party here!” off-handedly to a Comedy Central executive, and they were like, “Yeah, that would be awesome!” “Okay, well I’m going to go down this road now…” “Sounds great!” “I’m really doing it…” And what’s great about the show is it only takes two weeks to shoot. So you can be a degenerate for two weeks and still pull your life together after. Any more than that is too much, but I can handle two weeks. I was doing all the “Ziggy Zaggy, Ziggy Zaggy, Oi Oi Oi!” Man Show chugs when I was 16, and it’s really helped my tolerance as an adult.

Newacheck: Where we might take it next, we don’t know. Maybe a snowy mountain somewhere in the Alps or Australia, and see what kind of weird local comedy talent we can find. It’s a traveling circus without borders.

2012: Key & Peele

“I got a text from my manager. It just said, ‘Dude!’ with six U’s, all caps, and I think 11 exclamation points.”

Keegan-Michael Key (front), Jordan Peele (photo: Comedy Central)

Since 2009, viral-clip wellspring Tosh.0 has afforded online videos a televised platform for both ridicule and redemption. The America’s Funniest Home Videos/Talk Soup successor is not only cheap to produce, host Daniel Tosh’s observational invective is a proven draw for Comedy Central’s “males 18-24” demographic. Says Michele Ganeless, “The fact that it has been such a big hit for such a long time is a credit to Daniel’s ability to reinvent the show and keep it smart and topical and funny.”

But it was Keegan-Michael Key and Jordan Peele who, after winding down MadTV’s 14-year run on Fox, created a TV series that would itself go viral online. Key & Peele’s character- and impression-driven sketches mined the social gamut from pop culture and relationships to race and politics, often narrowing the divide between seemingly disparate issues—and people—in the process. UCB co-founder Ian Roberts co-executive produced, and Reggie Watts provided the theme song.

Over five seasons (aired across three years), Key & Peele scored the NAACP Image Award, a Writers Guild Of America Award, and Emmy nominations. “Their sketches evoke Dave Chappelle one minute, Sid Caesar the next,” the Peabody Awards body wrote of the show’s 2013 win. “They break new ground even as they lay claim to all of comedy’s traditions.

Wallach: Did Chappelle pave the way for Key & Peele? Maybe, maybe not. But Key & Peele is a great show. I have a 15-year-old son, and he was way too young to remember anything I did. But I can sit on the couch with him and watch Key & Peele.

Key: Jordan and I have the same manager, and one day he called us both separately and said, “Hey, I have a lot of interest between a few networks about you guys, and I was wondering what you’d think about doing a show together?” I was like, “Well, that’s an absolute no-brainer for me.” At the time I thought he was one of the best, and I since feel he is the best sketch writer in North America. I was like, “I’d be out of my mind to not work with him.” So we started to work on a show pilot together.

Alterman: When we first met with them they had an offer to develop at Fox. Myself, Jim Sharp, Gary Mann, and Monika Zielinska were all very passionate about them. No matter what form their pilot might take, we were convinced they belonged on our air. We just loved their point of view. The fact that they are both biracial—we knew that we would give them a lot of license to explore a lot territory that others wouldn’t have as easy a time exploring, mostly because they could explore it from their own genuine point of view. They probably had an opportunity to make more money in development to go to Fox, but anything on the networks is usually a longer shot. I think we really tried to press upon them that we were committed to getting them on the air, and that it wasn’t just about development.

Key: We were in kind of a bidding war between Fox and Comedy Central, and then finally Comedy Central said, “You know, we may not be able to match was Fox is offering you monetarily, but we can give you something that’s priceless, and that’s an opportunity. No matter what you want to do, we’ll support you. We’ll give notes, we can discuss it creatively, go back and forth. But at the end of the day, we will let you make the pilot that you want to make.” We thought, “We can’t pass that up. Let’s really believe in ourselves and feel like we can do this.” Comedy Central afforded us that opportunity, and they stayed true to their word.

Alterman: I think their original idea was Key Vs. Peele. They would take a topic, take opposite sides of it, and do sketches around that. There was another version: The Hypothetical World of Key & Peele. Ultimately what we really pushed was for them to just go right to the heart. In other words, if we had too much concept or premise to it, it felt like it might be restrictive. So we stripped it down to it just being, as simple-minded as it sounds, Key & Peele, so they could go anywhere they wanted to go where they had an impulse. We especially wanted them to go head-on into exploring racial issues, for example the fact this show coincided with when Obama became the first African-American president. It just seemed like it was so fruitful for them, and we wanted them to be sort of be unfiltered.

Kenney-Silver: We were out in Georgia for a couple of months shooting a movie called Wanderlust that David Wain directed, and Ken Marino and David wrote. Jordan was in the film in the same capacity that I am, as members of a commune. Pretty much every scene that one of us was in, the other one is in as well, so we got to know each other pretty well. The whole time, when we would do group stuff like dinner or go to the Cabbage Patch Museum, he would be going back to his little cabin to work. He was writing this pilot for Comedy Central with his friend Keegan.

Peele: I remember even working on my Obama impression behind the scenes.

Kenney-Silver: I’m like, “The two of you will be great. What is it? What’s it about?” In the back of my mind I’m also thinking, “God, I hope this goes for these guys. The reality is, most things don’t. I hope they just get past the pilot stage, because it’s such a nightmare and the industry is so flooded with comedy right now.” Cut to it being the next great comedy show that happened.

Key: I was doing P90X, just dripping in sweat in my living room, when I got a text from my manager. It just said, “Dude!” with six U’s, all caps, and I think 11 exclamation points. That’s when we first heard the show had been picked up based off the pilot, and that the focus groups were great. And all along the way, from day one until we decided to wrap the show, Comedy Central has been there to support us, every inch of the way.

Ganeless: I love those guys an unhealthy amount. They’re just the best. Not unlike Stephen [Colbert] or Jon [Stewart] or Amy [Schumer], they’re multidimensional. They are so super-talented, and they make things that are outrageously funny but have social commentary, which is a hallmark of our content. They’re just really good, super hard-working, incredibly smart, talented people.

Leggero: They were both very funny on MadTV, but Key & Peele is just at a next level. There’s almost a meta quality to it. I was watching the one about Urkel, and it was such a conceptual piece. Jordan is so talented, Keegan is so talented, and their sketches aren’t obvious. They really are going somewhere new that you don’t see on traditional sketch shows. You don’t see it on SNL. You don’t see it on MadTV. It’s not even hip. It’s just that there’s an intellectual quality to them. I always thought that because Jordan writes them and he’s such a good writer, he reminds me almost if someone like Louis CK were writing sketches. There’s often a deeper satire to it.

Peele: My real training ground was at Boom Chicago in Amsterdam, which is a comedy theater started by a couple of Americans from Chicago. I was there for three years, from ’99 to 2003. In a lot of live comedy, you develop a sixth sense for what an audience will laugh at. It was really helpful in the writing process. Not to say we won’t be surprised by how a sketch is received, but you begin to hear the laughter even when the audience isn’t there when you have a good comedic instinct.

Key: We both trained at the Second City, so I think part of it is that we try to look at every failure as a learning opportunity. There were a couple of sketches here and there that were big fat whiffs, big fat misses. But sometimes the sketch idea that goes by the wayside is the one that sparks the idea for a better sketch idea. At the end of the day, we just kept on trying to be positive about it and saying, “All right, so now we know what didn’t work there. Let’s build on that.”

Peele: I love the “Pizza Order” sketch, where I play Wendell Sanders and Keegan plays the pizza-delivery guy. “Meegan & Andre”—those were always fun. “The Valets.” I had a blast doing the “Continental Breakfast Guy.”

Kenney-Silver: They called Tom [Lennon] and I in together, and we were playing dogs in some field with other people. We laughed all day and peed ourselves. There are very few people on this planet as fun to work with.

Peele: Both of us were such big fans of The State. I remember being really blown away at how they were able to find a new style of sketch. If sketch were music, they would have been punk rock back in the day. So the ability to kind of pay it forward was more for watching their show when I was a teenager than even meeting them in more recent years.

Leggero: Again, when you’re around funny improvisers—same with Reno 911!—they make you funnier. It’s hard to imagine, because you think, “Oh, they’re gonna blow me away. I’m gonna be left in the dust because I’m nowhere near as good at improvising.” But the really talented ones, they elevate your performance. I just felt really honored to be on.

Peele: I think we knew pretty early on that with Obama and Luther we were nailing something that was nice and simple, but also something that rang true to people, especially at the time. There were certain things that people were uncomfortable talking about in the first year or two of Obama’s presidency. There was this hope that we would be in some post-racial world. When things came along that betrayed that, we initially kind of stuffed them under the rug because it felt like we were going backward. But Obama/Luther had a little bit of a cathartic moment for a lot of people: “Let’s just say what a lot of us are thinking through this character, and give the president the voice that everybody knows his internal monologue is.”

Key: When we did the very first Obama/Luther sketch, it felt like “Okay, we feel good about this, but who knows?” Kent Alterman got back to us the day after they put that thing online, and in a 24-hour period it got 1.2 million hits. At that point I wasn’t familiar with how many hits was good or over what rate of time on YouTube, but we knew it felt like we were onto something.

Peele: Early on, the “I Said ‘Bitch’” clips hit immediately. But we weren’t watching the online activity like it would be or could be the sort of phenomenon it ended up being. It really was a promotional tool for the show.

Alterman: We did have a strategy as we were going season by season. We put a lot of stuff online in the first two seasons, because we wanted to expose people to them as much as possible, and we saw how popular they were when we put sketches up that broke through. They got incredible traffic.

Ganeless: I remember the show really blowing up online. The ad campaign we did for season three was literally Keegan and Jordan doing a video for YouTube, saying, “Hey, this is a TV show!” People discovered that show in its pieces, and then came back to watch it on linear TV.

Alterman: Going into season three we held back a little bit. It’s a delicate balance where you want to market a show and get it out there where people are viewing, but we also want people to watch on the air. As they got more popular we released a little bit less of their videos online; that helps with the ratings.

Peele: Around season three, which is when “Substitute Teacher” and “East/West Bowl” hit—when it was clear that the online success was pretty substantial—there was the question of whether or not we were helping or hurting the actual show ratings by putting stuff online. Should we really limit what we put online, or does it ultimately publicize the show? We couldn’t see the direct result in the ratings, and the ratings did seem like they were successful beyond online.

Key: One of the big highlights was that first time you wake up in the morning and there’s, like, 60 emails on your phone that say “Congrats!” and you don’t know what it’s about. Then you find out you get nominated for three Emmys or five Emmys or whatever the case may be. And it’s all because of the hard work that you put in that somebody recognizes that. It’s a really good feeling.

Peele: It’s very, very validating. One goal with coming into sketch was reinforcing how important an art form sketch is. I’m in the school of thought that believes whoever ends up being the SNL castmember who portrays the presidential candidates has a direct effect on who gets elected. I think it’s such an important, influential sort of click track to what’s going on, and a mirror to society. So acknowledgement from the critics was amazing. But nothing feels better than the acknowledgement of people who approach us and say, “My whole family watches Key & Peele,” or, “I showed this sketch to my dad or mom or grandpa or sister or brother, and now it’s a bonding tool for us.” That’s really a special thing that transcends our highest hopes.

Key: Another highlight was that we found out the president knew who we were, and approved of the sketches. Him on Jimmy Fallon, saying, “Those guys are pretty funny,” it was like, “Oh my God, he knows!” Jordan called me, like, “Are you sitting down?” And somehow in the back of my head I already knew it was gonna be that. We would go to events and feel like, “The president must know. Somebody must have told him.” But we were so happy that that comedic premise worked out. We could keep going to the well with that one.

Peele: When Obama gave us a shout-out on Fallon, that was huge. And then obviously when he made Luther a real phenomenon by actually letting him translate him, that was absolutely crazy.

Ganeless: Luther was such a character, and the world was so ready for Obama to have that character standing next to him in real life. For them to have created that, when they finally met the president, it became an unbelievable moment in time.

Key: For us to literally be able to give the president a voice was—that’s ridiculous. I mean, that’s kind of almost why you say “no” to the show. The show’s got to be over.

Peele: We have the Key & Peele complete set now available through Comedy Central online. It’s the full realization of the fact that in some ways we are more of an internet show than we are a television show. We were sort of the first of our kind and straddled both, and now that every single sketch is online, we’ve done this interesting culmination that I think is really cool.

Alterman: Our site devoted to Key & Peele includes all of their sketches that were ever made, and people have the ability to cross-reference sketches thematically. They are continuing to have a robust life online, and we’re continuing to have various projects in development with them both as a pair and separately. They did five seasons of their show—which for a singularly focused, talent-driven show like that—for sketch, that’s a lot of seasons.

In contrast to something like like SNL, where there’s a constant flow of talent that goes through, but the show itself is kind of an institution. It’s more like Mr. Show With Bob And David. With Key & Peele we got five seasons from them, and we were really pleased with that. There’s not many sketch shows that are created, written, produced, and performed by the creators that have so many seasons. To this day, consumption of Key & Peele sketches is somewhere near a billion and a half views, so obviously they resonated with the world at large.

Next time: The final installment of our look at Comedy Central’s 25-year history explores Inside Amy Schumer, @midnight, Broad City, The Daily Show With Trevor Noah, further navigating the digital frontier, and more.