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Pop culture obsessives writing for the pop culture obsessed.

How Conan sketches are chosen and written

We may earn a commission from links on this page.

In entertainment, an awful lot of stuff happens behind closed doors, from canceling TV shows to organizing music festival lineups. While the public sees the end product on TVs, movie screens, or radio dials, they don’t see what it took to get there. In Expert Witness, The A.V. Club talks to industry insiders about the actual business of entertainment in hopes of shedding some light on how the pop-culture sausage gets made.

Second City alumnus Brian Stack joined Late Night With Conan O’Brien in 1997 as a sketch writer and has stayed with the show since then as a writer and actor. Stack frequently appears as a variety of characters, and is perhaps best known for his roles as politically incorrect ghost crooner Artie Kendall and the obnoxious Interrupter. Stack spoke with The A.V. Club about how the show’s sketches are written, produced, killed, or brought back, and shed some light on how some specific sketches were created.

The A.V. Club: What’s the schedule of how the sketches get pitched and written?

Brian Stack: We tend to pitch ideas every day; sometimes they’ll be off of a headline or some weird news story. For example, recently we noticed that there was a teapot that someone said looked like Hitler. I ended up doing a spokesman for the company that was showing other products they had. So what if they had, like, a fan that looked like a swastika. So a lot of things like that will come up the day of. But then other things will be pitched in advance and have a little bit more of an evergreen quality where maybe it’s a commercial parody or something that can go on at anytime. Other things are more time sensitive, and sometimes if you don’t get something on the day after a big news story, it feels too late.


AVC: So it typically doesn’t take more than a couple of days for a sketch to go from being accepted to being aired?

BS: Yeah, sometimes it’s literally the night after you pitch something, sometimes it’s the day of. We’ve had a lot of sketches that were pitched in the morning and done on the show. The upside of that is that you can’t agonize over it too much. I always liked Lorne Michaels’ quote about SNL. He said, “The show doesn’t go on because it’s ready, the show goes on because it’s 11:30 on Saturday.” So a lot of times on our show it’s like, “It is what it is. We’ll make it the best we can. We wrote it this afternoon and it’s going on the show tonight and hopefully it’ll work.” You can’t agonize over it too much, but it sometimes depends on how much editing is involved and how much post-production. When we used to do fake cable channels or commercial parodies, those usually require a day or two to shoot and edit and get the graphics, so it’s hard to them pull off in one day. But other things are written sometimes an hour before rehearsal. The more topical things that are ripped from that day’s headlines, those are sometimes written up until the last minute.


When we used to do what we called Clutch Cargo bits with the lips—Robert Smigel did about 80 percent of the characters and Brian McCann and I would also do some characters—those would be written up until show time. It would drive our script coordinators crazy because we’d be handing them last-minute changes. I know that’s how SNL works every week and it’s not usually quite that crazy on our show, but there are days when, especially in the Late Night days, when it was like Joan Cusack running down the hall in Broadcast News with the tape.

AVC: What’s changed with how the sketches get made in the various incarnations of the show? Were you allowed to take anything with you from Late Night to The Tonight Show to the TBS show?


BS: Technically, I think NBC owns all of those old characters, but I think if we were to do one of them again, we’d probably get away with it. But there’s a part of me that feels like it’s okay that we just move on. They never got too stale or too overplayed and I like to think we’ll come up with some new stuff that is just as well liked. It’s hard, though, because there’s part of me that would love to do an Interrupter again or a Crooner sketch again, but there’s also part of me that’s like, “Well, at least we never overdid it.” I get the feeling from Conan that we should just move on and come up with new things instead of the old things, even though we love them.

AVC: Does your stuff have to get approved by Standards And Practices?

BS: It rarely comes up. One time, Greg Cohen, one of our writers, had written something that dealt with religion. Standards And Practices had an issue with that, but over the years it hasn’t come up a lot. I think it’s because we were on late at night so they’d let us slide for the most part. Although every now and then early on there were certain issues that would cause concern. I noticed the subject of race, for example, was very touchy. At Late Night back in ’97, I’d written a sketch about an old baseball player named Whitey Phelps and it was part of a segment we did called, “Guests We’ll Never Have Back.” It turned out that the guy was a white supremacist. I had the crowd booing him and I was making it pretty clear that the guy was awful and appalling, but the very fact that he was a white supremacist—it makes people nervous. There are certain push-button topics that create a kneejerk reaction. In some ways I understand it, but in other ways I think it’s a shame. I think those topics should be talked about and that’s why guys like Louis C.K. are such wonderful comic artists because they bring these topics up and they do it in such a funny way that it’s palatable to people.


AVC: Roughly how many sketches get killed between rehearsal and getting taped?

BS: Usually with desk pieces where there’s a bunch of jokes—like for “Celebrity Survey” or something like that—we usually have quite a few more jokes in rehearsal than we do for the show. We know going in we’re going to have more than what will make a show. But, in terms of sketches, it really varies. There are some days where everything makes it in and then we have too much stuff and some of it gets held for the next day and then the next day it goes down in flames. Some days it’s 100 percent in and other days it’s 20 percent. And some days, it’s zero percent in and we find some way to salvage something from earlier to dump into the show.


AVC: Who has the final say?

BS: The final say is always Conan. He welcomes the opinions of our producer Jeff Ross or our head writer Mike Sweeney and Andy [Richter]. He really respects Andy’s opinion and Andy can definitely swing him one way or the other, but if Conan wants something in, it’s in, and if he wants something out, it’s out. Not in a tyrannical way, but he’s the guy who ultimately makes the decision about what’s on the show.


AVC: What sketches have involved the most work in terms of set design or costuming?

BS: The Galliano sketch is one clear example of that. There was another thing where we did a parody of the big Spider-Man musical that had gotten all that negative press; those tend to be very last minute and they had to create a lot of costumes. I was playing Doc Ock with metal ventilation tubes coming off my back so the costume designers had to scramble to get those things done. We did a thing called “Puppy Conan,” and they had to create a little mini version of our set with puppies running around, which was one of those things that the crew had to work overnight to get done.


I hate to say this, but there tends to be a relationship where the more work you ask the other departments to do, the less likely it’s going to make it on the show. [Laughs.] A lot of times, it’s the simplest stuff that makes it on. I always think back to Amy Poehler because the first sketch I ever wrote for Late Night was “Andy’s Little Sister.” I think that’s one of the reasons I ended up getting kept on the show, actually. I was originally just supposed to come out and fill in for three months. I had a three-month sublet and Amy knocked it so out of the park playing that character. I remember Conan saying, “You know, sometimes we go to so much trouble building these big sets and stuff and sometimes it’s a matter of getting the right actor, putting pigtails and headgear on her and getting the right performance.” A lot of the time, it’s the simplest stuff that scores the most. I’ll always be grateful to Amy for her performances in those sketches because I really do think that’s one of the reasons I was kept on. I was literally supposed to be there for three months until Tommy Blacha came back. He had broken his leg.

AVC: Another example of a simple one might be “FedEx Pope.”

BS: A lot of my favorite ideas at Late Night were complete accidents and that was one of them. Brian McCann used to put a VHS box on his head and be “VHS Corporal.” Then he’d put a FedEx box on his head and he started blessing us and was the “FedEx Pope” and we were like, “FedEx Pope! Why not?” So he ended up coming on the show with this white crappy bathrobe and these Chuck Taylors and it became this beloved character. It was just one of those wonderful little accidents that came from screwing around in the office. I was sitting next to Brian in a writers’ meeting just before we started and I remember shooting him in the leg and he started singing about having bulletproof legs, so I shot him in the chest and he fell over dead. So we were like, “That could be on the show tomorrow,” and it literally was. Neither of us would have thought of that at our computers. I think if you’re around the right people with the right amount of playfulness, a lot of wonderful things can come out just from screwing around.

AVC: Speaking of which, talk about the origins of “Slipnutz.”

BS: We did this back in the Late Night days. It was a very late night and we had no middle-of-the-show sketch for the next day. We just had nothing. And we noticed that the band Slipknot was booked for the next day. They’re this metal band that wears horror masks and there’s a horror-movie look to them. We just started joking around and wondering if there was a goofy comedy group booked for the same night by mistake called “Slipnutz.” So me, [Jon] Glaser and [Andy] Blitz started kicking around ideas and we just decided, what if it was three goofy guys that came out and poured nuts on the ground and then slipped on them and sang a song about slipping on nuts? So it was born out of a sleep-deprived desperation for a night when we just had nothing.


Amazingly, later on, we ended up opening up for Slipknot at the Continental Airlines Arena. It was very surreal to run out onstage when the audience didn’t know we were coming out. They hated us just as much as we prayed they would. We were kind of afraid that they’d laugh and enjoy it, but they were just throwing cups and giving us the finger. Andy Blitz said we should go out for an encore and I really wish we had, but we’d probably be dead now. Just before we went out there the stage manager said, “Be careful out there, guys. These fans throw batteries even at the bands that they like.” I’ll never forget running out on that stage in front of a stadium full of people who didn’t want us.

AVC: Did Slipknot ask you to come on?

BS: We asked them, I think through our music booker Jim Pitt. We went on before Slipknot and after Lamb Of God, who was their opening act. It was an introduction to this subculture I’m not real familiar with. I was amazed that a band that wasn’t all that mainstream could have an audience of that size. They filled this arena and they have this rabid following overseas. I’ve never been a big metal fan, but they put on an incredibly entertaining show.


AVC: You brought that sketch back several times. How do you know when to bring a sketch back?

BS: It usually comes down to how well it’s received by the audience and how much the performers enjoy it. It just feels pretty obvious that there was something there. We’ve had some things over the years that ended up being one-offs, but that was one of the things where it felt like it had the right kind of stupid. One of the highest compliments you can get from Conan is when he says live on the air, “That was so stupid.” That usually means that he liked it even though he’s acknowledging how dumb it was. So if Conan says, “Well, that was just too stupid,” that’s usually a pretty good indication that it’ll be back.


AVC: How do you know when to bring it back?

BS: There’s no real rule of thumb, but I think, in general, it was usually a month and sometimes longer. But in the case of the Slipnutz tribute album, it took a year to get all of those musical acts compiled together and we had to ask a bunch of musical acts and a lot of them turned us down. Like, Dolly Parton said, very sweetly, “I’m sorry, I don’t understand the idea and I don’t feel comfortable doing something I don’t understand.” I thought that was very refreshing how honest she was about it because you usually get a very vague yes then it would be a passive-aggressive thing where they wouldn’t respond like it didn’t happen.


It was such a thrill when someone like Patti Smith would be involved. I was so amazed because I always had this image of her as this very tough, streetwise rock performer, and in real life, she really struck me almost like someone’s daughter who was there for Take Your Daughter To Work Day. She was super-sweet and really shy. A lot of times people’s personas aren’t what’s underneath. There was nothing tough or intimidating about her in person. I was taken aback by that.

AVC: Who seemed to get quickest?

BS: John Mayer, of all the people I asked, seemed to be the biggest comedy fan. I was kind of astonished because he recognized me from the Crooner bit, but I was like, “Wait, you watch the show?” He’d remembered this bit that Glaser and McCann had done called “The Copywriter’s Cage Match” which was one of my favorite little one-off bits. I couldn’t believe he knew that bit. It made me realize instantly, “Oh my God, this guy is a real comedy fan.” I was just as surprised when Jack White turned out to be such a huge comedy fan. I wish we had asked him [to do Slipnutz] but I think at the time The White Stripes weren’t that huge. Conan was in a White Stripes video, and he wanted to talk to Jack White about the blues and guitars and stuff and all Jack White wanted to talk about were chimp suits. I think some of these guys are huge comedy nerds. John Mayer, more than anyone we dealt with, seemed to be the biggest comedy fan out of all of them. Los Lobos were just nice enough to do it even if they didn’t quite understand it and Steve Winwood was nice enough to do it. But John Mayer was a guy that was very familiar with our show. And sometimes you feel like you’re just doing this show for yourself but then you forget that people actually see it. Just his familiarity with some of our more obscure bits was a real surprise.

AVC: Let’s talk about “The Interrupter.”

BS: Conan would often joke around when we’d be pitching middle-of-the-show sketches that a lot of them involved him being interrupted. Like with a prospector: [High-pitched voice.] “Gold!” He’d be in the middle of a sentence and a character would just pop out of the audience or pop into the door. So one of our writers, Michael Koman, who was the co-creator of Eagleheart and is one of my good friends, had the idea for me to be this character called The Interrupter where we would just hit the nail on the head. This is a guy who isn’t just interrupting the show, but that’s his sole purpose. So it was initially a commentary on a cliché on our show and it evolved into the Interrupter having this ever more horrible life that he was gleefully okay with. Seven different types of hepatitis, he lived in a dumpster behind the Port Authority—it got more and more fleshed out. And so that’s still one of my favorite characters and sketches we ever did because it grew organically out of something very real and the fact that I loved cutting them off in mid-sentence even though it was at my own expense. I was always revealing something negative about myself, but in a very upbeat, happy way.


AVC: How did the costuming get chosen for that character?

BS: I think that was Michael’s idea. I think he wanted almost like an 18th-century look. It ended up being almost a weird, foppish, aristocratic outfit and I think it even had a cape. We wanted a look that would reflect that this guy completely has no contact with reality.


AVC: And then the voice, did that just come out of you right away?

BS: I don’t know why I came out with that particular delivery, it just felt right, I guess. We didn’t know exactly what he should sound like, but what came out seemed appropriately psychotic.


AVC: Who is the actress in this particular version?

BS: That was actually my wife, Miriam. That was the only Interrupter sketch she ever appeared in. That particular one is probably my favorite out of all the Interrupter sketches we did and the fact that Miriam is in that one is a nice bonus.

AVC: There’s a lot to unpack with this Poseidon clip. Can you set the scene and tell us what we’re seeing here?


BS: It shows a glimpse behind the scenes of rehearsal and how things don’t often make it to show and how we have fun while not necessarily working. We did the Poseidon sketch, which I have to say I still really enjoyed, but it didn’t end up making the show. We had recently done a sketch called “Minty The Candy Cane who’d briefly fallen on the ground” and he had things stuck to him. So he got a wonderful response from the crowd and I’d sung Minty The Candy Cane’s theme song through an old microphone so it sounded old. “When the holidays come along, you can hear the sound…” It was kind of that old sound and Todd Levin, one of our writers, had asked me to do it because Minty was his idea. I think there were still residual good feelings from the Minty song, so we did a command performance while dressed as Poseidon. Poseidon almost made the show, but I think it was cut for time. I was dressed in the full outfit and Roger Waters from Pink Floyd was the next guest and I saw him being led through to go on and I was like, “Oh, I guess we’re cut for Pink Floyd.” Which isn’t a bad thing.

AVC: What was the sketch?

BS: If you notice in the background behind Conan’s desk there’s this huge ocean and I just had the idea of Poseidon coming out of that ocean and screaming out something. I don’t even remember what it was. The idea for Poseidon originally came from my old Chicago improv days at Second City. It was something that we did back in ’94 or something and I remember just having a lot of fun being this big, blustery sea god. They built a wonderful tail for me in the costume department so I’m still a little bummed out that it didn’t make the show, but a lot of things that we like don’t necessarily get on. I know it’s like that with other shows, too. I remember watching SNL rehearsals on our closed-circuit TVs in 30 Rock and just laughing to the point of tears at sketches that didn’t even make the show. I realized how subjective that stuff is. I saw Will Ferrell do a doctor sketch that wasn’t on the show and the next time he was on our show I was like, “What happened to that sketch?” and he said it didn’t get a peep at dress rehearsal and I thought, “Really?” You just realize just how totally subjective comedy can be and a lot of times things that appeal to comedy writers don’t appeal to the public at large. But it’s a matter of personal taste, I guess. 

AVC: When something doesn’t make it like that do you ever try it again?


BS: Sometimes we’ll try to rework something a little bit, but a lot of times if it doesn’t make it there tends to be a “well, we tried” and it doesn’t really come back. I think there have been some cases where we brought things back and tweaked them a bit to shorten them. But if everyone really loves something enough, it might be one of those things worth salvaging, but if usually something just dies, it dies. At rehearsal once I did a sketch inspired by Orson Welles’ film version of Kafka’s The Trial and it was one of the few times I ever remember hearing absolutely nothing from the audience.

AVC: But everyone can identify with that premise, right?

BS: Oh, yeah. [Laughs.] Rarely does a sketch make it on a show where we’re that wrong. Conan just liked the sketch and thought it was really fun and weird and the writers all liked the sketch but it was so weird to just hear this deep-space silence. That’s one of the few times a sketch was fully pulled from the show even though we all liked it. I guess it was too dark or weird.