Pete Holmes picks his favorite You Made It Weird episodes

Pete Holmes picks his favorite You Made It Weird episodes

Bestcasts asks podcasters to discuss the three most memorable episodes of their podcast. Note: Ties are allowed/encouraged. 

The podcaster: Pete Holmes has been a stand-up comedian for years, but he seems to have really burst into the general consciousness with the 2011 launch of his podcast, You Made It Weird. The semi-weekly, always-lengthy, one-on-one interview show finds Holmes chatting up fellow comedians and friends, talking about everything from masturbation to whether God exists. Holmes has embraced the format to spread his open personality to the masses, sparking legions of self-described “weirdos” to come to his shows, give him big ol’ bear hugs, and preach the gospel of the comedian with the youth pastor face. That audience will hopefully follow Holmes to TBS, where he’ll host a nightly chat show beginning this fall.

Episode #22: “Emily Gordon”
Pete Holmes: It’s really bizarre that is still my favorite out of all of them, because I’ve had some people like Jon Hamm and Judd Apatow on the show, but my favorite episode is from the wife of a comedian. She’s not a comedian herself, so she’s a little bit of a betrayal—not a betrayal, but a deviation from the theme. But you can just listen to me getting my mind blown because she’s one of the funniest, smartest, wisest people I know, which is remarkable. A big theme of the show in general is who is right for a comedian romantically. She been in this successful, flagship relationship that everyone looks up to, and for her to share her thoughts on how to have this successful relationship when you’re in this misfit lifestyle was just incredibly valuable. I honestly think that episode has helped people’s marriages. I have had people open up for me over the years saying, “I’m struggling, I don’t know what to do; my wife is freaking out that I’m on the road,” or “I don’t know what she needs me to do for her or her for me,” and I tell them to listen to that episode and get back to me and they’re like, “Yeah, that blew my mind.” So I can’t take credit for it. She’s just a remarkable person.

The A.V. Club: You two were friends before you talked on the podcast. Had you had these conversations with her before, or did this just blow things open?

PH: Well, that’s what is so amazing because it is a whole new level. That’s such an amazing gift of the show for me because it gives us this great excuse to hang out for hours. If I invited someone to come and sit in a small room with me and talk, it’d be awkward, but if we record it, it’s suddenly okay. Then everyone is more aware that it’s being recorded and they’re going to kind of be at the top of their game, and you have these really deep conversations with wonderful people that, in the case of Emily, I’d known for years, but I didn’t know how wonderful a person she was, really, until that conversation. It helps me to get to know a friend better. 

AVC: She reveals a lot of personal things about her coma and her divorce. 

PH: It’s a weird phenomenon. I liken it to—I got this from NPR—there was this guy talking about why people share so much on reality shows. And there’s a little bit of the Kiss Cam philosophy going on. He tells the story of swapping seats with his buddy and his fiancée and the Kiss Cam—which his buddy and his fiancée had agreed to beforehand—zoomed in on them. So this guy and his friend’s fiancée, with the pressure of people watching and all that sort of stuff, suddenly there’s an expectation and he kisses his friend’s fiancée.

With the show, people start revealing things that they wouldn’t reveal otherwise without the Kiss Cam phenomenon. Nobody really regrets it, either. It goes both ways; it helps people open up, and it also helps people feel okay about opening up, because it’s just this understanding about what the show is, you know?

AVC: And because you’re so open, it helps.

PH: That’s the big trick. I’m not shy about that.

I tell people on the show all the time that I open up and it helps if you open up. It’s not a trick and if you tell people that, it works. Emily was very open, but some of the better episodes require a bit of coaxing and the full-proof way to do that, if you want to get an embarrassing jerkoff story about them, is to tell an embarrassing jerkoff story and they’ll want to keep up. [Laughs.]

AVC: Since Emily’s not a comedian, did you approach her episode differently than the one where you talked to Kumail Nanjiani, her husband?

PH: Yeah, a little bit. I approached it the same way I approach Emily in real life: I go to her for help. We all do, because she has a therapy background and her entire community of friends is comedians. Emily has a very easy position in life as the unofficial therapist to everybody. We met right after my divorce, and that was the kind of perfect cosmic timing to meet her because she has seen me through that big thing and other tiny little things. Like— we talked about this on the show— if some girl is not replying to an e-mail I wrote her, I call Emily. That’s what she’s there for.

The reason Emily is different is not because she’s a comedian, but because she’s a friend of mine. So an episode with Kumail, even though he’s a comedian, is in that category, you understand? For an episode with Zach [Galifianakis], we’re not close, we’ve never gone to dinner or anything, so you approach that a little more carefully, a little more premeditated, but with Emily I just went in and knew we’d have stuff to talk about.

AVC: Did it change your relationship afterward? 

PH: It definitely made us better friends. It’s this weird sharing of the fan base. I know that’s a weird thing to say, but when you have someone like Emily on the show, I’m vouching and saying she’s remarkable, and that’s kind of true of all the guests. She gets to enjoy it, and now people know who this exceptional person is. Where she used to be this person behind the scenes, now when people go to Meltdown—not just because of my podcast, but because of her own podcast and her involvement with that live show—people get to know who she is.

One of my favorite things is you take someone like Kurt Metzger, who doesn’t really run in the same scene with me. He’s a little bit dirtier, a little bit clubbier, but he’s one of the funniest people I know. He’s not really aware of my weird, nerd-culture experience. But then I have him on the podcast and he does it just because we’re friends. Then afterward, he’s like, “People are coming to the shows just because they heard me on the podcast.” And I’m like, “I told you.” This is the thing when you get to share this wonderful, gracious, open, friendly, sweet fan base that I’m very fortunate to have. If Anthony Jeselnik tweets something that involves me, I know for the next six months I’m going to get shitty tweets sent to me. Whereas my fan base is like, “I made you cookies!” You know what I mean? I prefer that.

Episode #139: “Bert Kreischer”
AVC: During this episode, you said it was as if you were dancing with each other.

PH: Well, I didn’t know Bert at all, but it goes back to that excuse about getting to hang out. People were tweeting that Bert should do the show because we have similar laughs and similar energies. I’d never met him and wouldn’t have necessarily had a way to sit down with him as long as I did. He’s got a family, he’s touring a lot, but by virtue of having a show, we got to sit down and the fans of both our shows were right when they predicted we’d have a really good time. 

There are a couple shows like that I call “first date” episodes where the first thing you talk about is “nice to meet you.” Aisha Tyler was the same way; I’d never met her, but we just hit the ground running and there’s a really special—like Bert said—sort of a dance energy to it where you’re falling in comedy love with the other person and I think that can make for some, hopefully, compelling listening.

AVC: Why does something that Aisha Tyler episode stand out for you?

PH: It’s because I’m trying to manufacture a sleepover feel; like a tree house or a clubhouse. I want people to be silly and play and feel safe and some people, you have to coax them into that space and some people bring me further into that space, even past the point that I wanted to go. 

If you listen to the Bert episode, one of the games we play in that episode toward the end is where we sing along to a pop song that we don’t know the words to. Bert was like, “Let’s do that to this other song,” so we were singing other songs. [Laughs.] He took over as co-host of “The Joy Show.” That relieves my responsibility as host to keep the show going, I don’t have to think of what we have to talk about next, and that helps me be present and be silly and, hopefully, that helps the show be funnier because you have two people playing instead of one hosting and one playing or whatever.

When two energies come together and make this salty/sweet combo, it was a surprise. You can’t manufacture that novelty of “Holy shit, this is my kind of person!” But when you capture it and get to record it, how special is that? How many people who are a good friend of yours would you want to be able to listen to the first time you met? I’m privileged to have all these recordings. Like this is the first I talked to you; here it is. And look at how fun it was. They’re treasures. I often think about being an old person and listening to these shows, and I definitely think it’s something that I’ll do. I can’t listen to them now—I’m too close to them—but I’ll show them to my kids because I would like them to know what their father was like without any sort of parental filter. Now my kids will be able to be like, “Oh, this is exactly what you were like when you were 33 and an idiot.”

AVC: It’s almost like you read your diary into a tape.

PH: I have a terrible memory, and there’s a real need to record and chronicle the things I’m doing, because people will be like, “What did you do yesterday?” and I’ll honestly have no idea. I will have just taped a TV show or something. The bridge is just burning behind me, and the more I can record or write down and make a record, it really is the perfect job for me.

AVC: When you and Bert were singing, that joy really was contagious. It made me think, “I should play this game with my friends.”

PH: I’m so happy to hear you say that, because if there was a mission statement to the show, one of them would be that it’s okay to give yourself permission to have fun. I know that sounds stupid, but, as grown people, we’re often in our own way to have a good time or to be silly or happy. So when you have two grown men singing Ke$ha and laughing so hard at themselves, you either like it or you don’t. I have some people that can’t stand that I laugh at myself, but I’m like “Go fuck yourself. I’m having a good time. Either get on board or listen to a different podcast.’ This is going to be the silly, happy, fun time.

When I pitch the show to people, one of the words I use when I try to get them to do it is “safe.” This is the “safe” show. Whatever you do is okay, whatever we say is okay, and whatever games we decide to play will be okay. We’re trying to manufacture a loving environment where whatever you say, I have your back and you have my back. That’s a little bit of an improv background, but it’s also a little bit of a guy who just likes to be silly. When people listen to the show, and I get this from time to time, they’re like, “I now sing along to songs I don’t know in the car” and I’m like, “Yeah. That’s exactly right. And so do I.” I’m trying to, with my stand-up and with the podcast, give people these little stupid things to give them happiness. I know that sounds lofty or like I’m starting a cult, but I kind of feel that way.

AVC: You bring peaks and valleys to the show, though. You talk about serious stuff and silly stuff in equal measure.

PH: I think that’s one of the phenomenons of the show. The show has a reputation of being a silly, happy, joyful time, but if you ask a diehard fan of the show, they can tell you grotesque details of my divorce or stories of my lowest point or of a guest that contemplated suicide or had an eating disorder or was depressed for three years. Or, in the case of Emily, being sick and being in the hospital and having everyone she loved thinking she was going to die. So all this stuff is in there, but the overall takeaway, hopefully, is a silly, happy fun place. But then, if you listen to what we say, we swear a lot, it’s dirty, we talk a lot about fucking, we talk a lot about death, we talk a lot about fear, and we talk a lot about loss. All those things are in there, but, at the end of the day, the impression it leaves you with is “let’s be silly,” I think.

AVC: The show’s also relatable. You might hear someone you like talking about something that happened to them that also happened to you.

PH: I think that’s what makes it positive. I’m thinking of Sean O’Connor telling a story on his episode that he’d never told before about losing his brother at a very young age and how a story like that could be positive. And it’s positive because of what you said, that if you also lost a loved one or a family member or—I get this a lot because it’s my big thing because I was divorced—I get a lot of divorcees coming up to me, a lot of people who got married really young emailing me. So it’s the really dark stuff that gets a light spin because it’s unifying, it’s solidarity. You hear a lot of stories about people going through the same thing and your feeling at the end of a sad story can be positive. 

AVC: You approach it in a safe way. You talked to Jon Hamm about his parents dying at a relatively young age, but you didn’t press him about it. You gave him the space to talk.

PH: There’s a balance between knowing the path of least resistance vs. knowing to push or knowing when to not pursue a certain angle. I know when Dane Cook did the show, a couple of controversies came up and it was very deliberate to avoid them. I know people listening to the show were like, “Is he going to talk about the stealing material from Louis [C.K.] fiasco?” I don’t really care and I’d rather talk about certain things and if Jon Hamm wants to talk about his parents and what that made him feel, it’ll come up once you establish the feel of the show. But I tell them all the time—usually on-mic because we don’t talk off-mic at all—the show is called You Made It Weird, but you’re not supposed to feel uncomfortable or unhappy at the end. We should both feel really good about what happened. 

AVC: You’re also in the same room. Giving someone a hard time is complicated when you’re two feet away from them.

PH: Yeah, totally. I always say it’s not Hard Copy, which is a weird ’90s reference. 

The show is called You Made It Weird and I realized that just by being myself, the thing people find weird or uncomfortable about the show is that I’m following my natural instincts. I didn’t even think that was strange but then people are like, “You laughed.” It’s okay; we’re all weird.

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AVC: Do you come out of the episodes better friends with the guests? Like on the Bert episode, you were talking about going to Kurt Braunohler’s skywriting party, and he said he wanted to go with you. Did he?

PH: No, we didn’t go to the skywriting party. That’s actually an interesting question. The truth is, a lot of the time, that’ll be it for a long time just because things are so frantic; I’m talking to you from San Francisco right now. I go to L.A. for one day on Monday, and then I go to New York, then Cleveland, then Philly, so there’s a lot of traveling around. So, often times, the podcast is how we hang.

Duncan Trussell is one of my favorite people ever, and his episode is one of my favorite ever. It was a conversation. We talked a lot about spirituality, and it really turned my life around in this amazing way. I have Duncan’s phone number and he lives about 10 minutes from me, but when we hang out, we typically want to record it. It’s this weird sort of Phillip K. Dick science-fiction future where people only hang out in front of microphones. That’s not always true, though. I see Emily, I see Kumail, I see my friends, I see Jeselnik, but I don’t necessarily have time to follow up with the people I want to follow up with. Again, it makes the podcast that much more precious.

AVC: That’s also the burden of being an adult. 

PH: That’s exactly what it is being an adult. The difference is, when you’re a kid, your parents set up these play dates. If you enjoy your time with Bert, let’s set it up again. I need some sort of assistant to help me maintain friendships.

AVC: Then again, having too many friends is a pretty choice burden to have.

PH: That’s a wonderful problem to have, and the weirdest thing is Bert has a podcast. It’s sort of an L.A. thing and I think that’s why L.A. produces so many more podcasts than New York. In New York you would run into people and hang out more, and there’s public transportation and all that stuff. But in L.A., when I start thinking about how much I want to see Bert again, I know it’ll happen because he has a podcast. I’m trying to get Kevin Smith. Somebody was like, “You guys should just hang out,” and I’m like, “Well he has a podcast, and he’ll do mine. That’s like six hours of hang out.” But Bert’s episode was almost three hours I think and most people, in a month or three months, don’t talk non-stop looking each other in the eye for three hours in a quiet room. I told you I’d known Emily for years, but before the podcast, I didn’t know so many things about her. So it’s almost like science-fiction meal in a pill; it’s friendship in a pill.

Episode #96: “Zach Galifianakis”
AVC: You didn’t know Zach Galifianakis very well beforehand, correct?

PH: Yeah. The reason I listed the Zach episode is because he tends to be a very private person, and we got into some rarified air for a couple of reasons: One is because we knew each other from the comedy scene a little bit and I also just caught him at a really good time, I think. He’s such a sweetheart, I don’t think you’re ever going to catch him being a dick. We set it up at his house and his wife was there and he was clearly having some lovely morning and was drinking coffee and I just came in and started recording this very surreal experience. I’d never been to his house, I’d never met his wife, and had probably talked to him 15 times in my life and here we are sitting down and, again, we’re going to talk for a couple of hours. So the fact that it goes well and he’s showed this side of himself that I don’t think he normally shows is one of the reasons I’m really proud of that episode. 

A lot of people comment that when Zach does an interview, it’ll be a lot of bits. I actually talked to him afterward, and he said he was planning on giving me a fake answer to a question. But then what ended up happening is he gave this sincere, funny, not at all forced, genuine, silly, sun-soaked conversation that I’m really pleased with. It’s almost like you’re getting a guy of that caliber with that sort of public… I’m trying not to call him a star or celebrity, but that’s basically what I’m saying. If you can have a real conversation with him, I’m really proud of that. And I think, in the end, he enjoyed it and mentioned it several times and that’s the perfect show for me: if we can sit down and we both really enjoyed it and not have any regrets or anything. 

AVC: You also weren’t really forced to talk about whatever he was promoting at the time.

PH: That’s some stuff I’d like to take into the talk show that I’ll be doing after Conan [O’Brien]. Conan just sent me to London because I interviewed [The Fast And The Furious 6 stars] Vin Diesel and Michelle Rodriguez and Paul Walker there, and I know, I get it, you have someone on and they talk about the movie they’re promoting; that’s what they do. But the whole time I was thinking, “I’d really like to know what Vin Diesel is afraid of.” [Laughs.]

Wouldn’t that be interesting? And that’s just how I am. Some people when they make small talk, and I’m not looking down on this, they want to talk about sports or cars—I know I just picked two sort of manly things, but those aren’t my things—I’ve always wanted to know if you have any reoccurring dreams or any feelings on aliens. What happens when we die is a huge one for me, were you raised religious, how did you lose your virginity. I always want to know that sort of stuff because those are the things that concern me. But then you take someone like Zach or, hopefully in the future, Vin Diesel or whatever, it adds an extra layer of satisfaction that somebody who is a public person and kind of values his privacy opened up a little bit. I think that was really special.

AVC: Hearing bands talk about their records is the most boring thing in the world.

PH: And you’re the fifth person to have asked them that, you know what I mean?

AVC: But asking them, “I hear you like baseball” is much more interesting, because that’s something they might actually be excited to talk about.

PH: That’s exactly right. You have to find the right counterpart to that sort of interview. Some people just don’t want to do it, and some people just aren’t right for the show or an interview like that. I’ve had some really wonderful people decline doing the show because that’s not their kind of thing. We’ll agree to do it and we’re friends, and I’m like, “We talk about comedy, sex, and God.” And they’re like, “Nope!” [Laughs.] They have no interest in opening up that way.

AVC: As we get older, we don’t have these conversations. When you’re in college, you’re talking to strangers about whether or not they believe in God. Now if you bring that up to someone, they’re like, “Where’s that coming from?”

PH: It’s funny you said that because I’m working on a bit right now about how when I was a kid, the books I took out of the library were about magic and hypnosis and the galaxy. And, unfortunately, the requisite of growing up is that you check off having those certain conversations. I think that’s one of the things that makes the show so compelling is that you’re with someone like Jon Hamm and you say, “Do you believe in God? Tell me why or why not and when you do or don’t.” Let’s be kids again. Let’s talk about what the fuck is going on here instead of being so used to it. We’re on a planet. This is so absurd. What are we doing here? I need to talk about this, which is really an extension of my anxiety. I need other people to see the zombie so we can commiserate on how weird this life is and I feel better and then we do it again. 

One of my obsessions in life is that we have the tools to manufacture moments and real things, but it’s overwhelming and there’s a lot of fear and you think maybe you’ll be rejected or embarrassed or somehow hurt emotionally. So we don’t do the things we know we can do, but we can make people feel better and make people happier with compliments or just being positive and that sort of thing and sending it their way. We also have profound little moments, but it’s hard. It’s so much easier to eat a taco and jerk off and go to a movie. I understand because I do that most of the time, but this show has become a vehicle for me to have the kinds of conversations I’d like to be having. And when I hear you say you listen to these conversations and then go home and have more of them, that’s the juice. That’s good stuff. It’s become about so much more than proflowers.com or selling tickets on the road; it’s actually about making life better. I know it sounds like I’m so up my own ass, but I don’t care. [Laughs.]

AVC: My dad is always telling me to ask interview subjects who is the most famous person is they’ve ever met, which I think is a good conversation starter. 

PH: That is a good question. He’s smart because people are always so excited to tell those stories. That’s why it took so long for me to find the virginity question. That worked really well with Bert because he had a great story. If you ever want to get someone going, ask them about their virginity or their first kiss or something. But meeting a celebrity is also a good one because it lights people up.

AVC: It’s always something weird, like, “I sang with Sting.”

PH: I knew a guy who shared an elevator with Will Smith and it was like 30 seconds in real time, but the story took about 20 minutes to tell.

AVC: Do you feel pressure to make your podcast shorter? Surely you’ve heard complaints about it being too long before. 

PH: [Laughs.] Yeah, I have. It’s subjective, I guess. Some people might have thought that even the best episodes dragged or found one that I thought was too long was too short. It’s an interesting thing, because I can’t always be like, “Fuck you. It’s my show.” The audience does have a say in what the show is, and that’s something that I’m kind of learning. It’s like George Lucas: He goes back—I know this is kind of pretentious to compare my show to Star Wars—he was like, “Fuck you. I’m going to go back and remake the first three films and edit it so that Greedo shoots at Han first rather than Han shooting at Greedo for no good reason.” Fans were so mad, but he was like, “Fuck you. It’s for my own imagination.”

But the real lesson is that the fans do get a say for better or worse. They do get a little bit of a vote in terms of the length of the show or if I talk too much or should I laugh less, which is another one I get. I don’t know who these joy police officers are. Some days, I’m like, “Fuck you. Turn it off when you’re done. If you want to pretend the podcast is 90 minutes long, at the 90-minute mark, pretend I said, ‘Well, that’s all the time we had.’” That’s how I feel when 60-minute podcasts end. I’m like, “Wait, it’s over?” When Alec Baldwin interviewed David Letterman and Letterman said, “That went by quickly; I can’t believe we’re done” I was like, “Don’t be done. It’s David Letterman. Keep talking.” By the way, I’m not shitting on Alec Baldwin, I thought it was a great episode, but I would never do that.

So to answer the question in one part, I do feel a responsibility to make the show somewhat consistent to what people are liking, but I get a lot more people saying they like the show long—way more, it’s like 5-to-1. For every one person that says it’s too long, I get five who say, “This is how I get through my work day. Please make them longer.” Again, this sounds kind of big-headed, but I think it’s so fucking stupid to go against the spirit of podcasting completely to say, “I do a 60-minute show.” What the fuck are you talking about? Why would you do that? You don’t have advertisers, you don’t have a network, you don’t have someone to answer to, you don’t have network notes, you don’t have studio notes, you’re doing a show. It’s punk rock and end the podcast when the podcast is over. It’s like fucking: Don’t stop till it’s done. “I fucked for 60 minutes. Letterman wants to fuck more, Alec! Give him another toss!” And if some people think that’s too long, some people don’t like long sex, either. I get very worked up talking about this.

AVC: Roman Mars from 99 Percent Invisible gave this speech about art and design that was interesting. In it, he said that designers and architects have to deal with putting something out into the world and then realizing that people use it differently than it was designed or how they’d imagined people would use it. The same thing would apply to podcasters or comedians or writers, probably. You put something out that’s in your head one way, and then someone hears it another way.

PH: That is interesting. I think, in terms of the show, I didn’t think people would be using it at jobs where they were lacking human contact, but that’s one of the beautiful things about it. I’m using the show to connect with people and people are using the show to connect with people because they feel they work at a job that doesn’t let them talk to other people. They’re at lunch and they’re just kind of quiet. [Laughs.] But, yeah, I can’t really control what people are doing with the show, I guess.

AVC: Have you noticed a big uptick in your stand-up attendance and things like that from Weirdoes?

PH: Oh, yeah. One of the best things about it is that I used to do stand-up and try to win people over—and I still do shows like that sometimes—but rather than having a show where people are like, “Let’s see if this guy is any good,” it’s, “Oh, we get to hang out with our friend, Pete.” Because you really do know me pretty well, you know what I mean? The seduction is over. They’ve probably already made up their minds of whether or not they’re on board, and then we get to enjoy an evening of jokes together where I’m not really persuading them but hanging out which is a dream come true.

But in terms of selling tickets on the road before and after, there is no comparison. There was none; now there’s a lot, which is unbelievable. You think people are going to see some stand-up special you did or some late-night spot and it’s never that. It’s the podcast, and I’d rather it be that. Bill Hicks has this great quote where he says, “Less jokes, more me,” and that’s what I want, too. I’m not a salesman going around trying to sell jokes to strangers. I’m trying to go around and hang out with the people that want to hang out with me and have a nice time.

AVC: Is that how you always approached stand-up?

PH: Absolutely. That was a big thing when it turned so it wasn’t me against the audience. Now it’s just me inviting them to enjoy what I enjoy. Some of the best stand-up shows I’ve ever had were for Weirdoes. And hopefully it’ll always be that way.

Filed Under: Comedy

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