Pete Holmes is returning for another season of his semi-autobiographical HBO series, Crashing, about the early days of his stand-up career. And, like Season 1–which featured an impressive revolving door stable of great comedians like Sarah Silverman, Dave Attell and Artie Lange–Season 2 promises even more guest stars from the comedy world like Penn Jillette, Doug Benson and Gilbert Gottfried.
AiPT!, along with a few other news outlets, had a chance to attend a January 9 press event with some of Holmes’ supporting cast: Jamie Lee, a stand-up comedian who was a Season 1 writer and is now also joining the on-screen cast in Season 2 as a female lead; sketch and improv performer Zach Cherry who quite memorably got Spider-Man to do a flip last summer in Spider-Man: Homecoming and then tried to parlay that cameo into a spin-off film in a recent appearance on The Late Show with Stephen Colbert; and stand-up comedian Rachel Feinstein. Below is a transcript of the conversation.
Question: Who are your comedy heroes? Did you have heroes in the beginning of your careers?
Rachel Feinstein: I liked to watch the old Tracey Ullman stuff. I was really into her. And Joan Rivers. Loved Chris Rock.
Jamie Lee: This sounds kinda nuts, but Miss Piggy was honestly a big one for me because it was what she said. They wrote really funny stuff for her. But also, all of her mannerisms were, like, legitimately the funniest thing. And I love how she’s, like, always mad.
Rachel: I agree. There’s something very funny.
Jamie: And, when I watch it, there’s actual, like, amazing comedic timing in everything that she does and says.
Zach Cherry: Miss Piggy also.
Rachel: But yeah, it was fun just watching when you were a kid to see somebody do something heinous. I felt like, as girls, we weren’t supposed to be heinous. So it was very exciting on TV. I’m like, wait. She’s being actively disgusting. Maybe I can be too.
Jamie: I think you’re touching on it because yeah, that’s like, that’s exactly what it is. Like, I remember, in Muppets Take Manhattan, when she, like, took that guy’s roller skates to catch up with Kermit and, like, spied on him, there’s just, like, that shot of her, like, rollerskating through Central Park. It’s like, such a classy surrounding and she’s just like, “GET THE FUCK OUT OF MY WAY!” And you’re like, this bitch is amazing! Like, that’s incredible!
Rachel: Yeah, even seeing a woman in a rush.
Jamie: Yeah, bitch in a rush!
Rachel: I love a lady in a rush. Just a real slovenly reality of being in a rush.
Zach: I mean, besides Miss Piggy, South Park was a big thing for me growing up. Will Ferrell I love. I think he’s so funny. Every time I try to think about heroes, I think of, like, Nathan Fielder, but I didn’t know about him when I was coming up. But it’s hard for me to, like, remember past what I’m currently loving. Nathan Fielder and Miss Piggy are my answers.
Question: How much of your own material, stand-up or otherwise, do you bring into your respective roles on the show?
Zach: I bring none of my material. There’s a little bit of my, like, personality in my character.
Jamie: Zach, I think your riffs make it into the show more than anybody else’s.
Zach: I bring the riffs.
Jamie: And he is a brilliant improviser. And I feel like a lot of riffs get cut out, and you riff a lot. And then it stays with you.
Rachel: You have an ability also to say, like, a vaguely insulting thing but make it seem like it’s just a fun-loving comment. You’re really good at saying something that’s kind of like friendly and eviscerating.
Zach: Never my intention.
Jamie: In one of the later episodes, I feel like our characters, my character and your character are, like, secretly sparring.
Zach: Yeah, or competing.
Jamie: We’re literally, like, we hate each other but it’s kind of sweet. It’s really funny because it’s not like a deliberate fight.
Rachel: There are a lot of things like that in Crashing, I guess. Like, you act like you’re actively insulting somebody but it–and for no particular reason, that you’re basically very fond of.
Jamie: You actually really like them. You just want to eviscerate them for your own purposes. For fun, let me just destroy their self-esteem right before they go up. A lot of, like, my older stand-up is in the show because we tried to capture that slice of life from, like, when you’re first starting out. And those were the jokes that I was telling back then. But then we also wrote some new stuff. And especially, for one of our latest episodes–it’s the same one I was talking about with Zach–where we actually go out of town and we’re performing for, like, a new demographic, to not give too much away. And the jokes for that episode were really specific to that experience. So I feel like the writers and I were trying to craft material because it was not stuff that I had in my act.
Rachel: I don’t really do my stand-up in the show, but it’s definitely my life. The nice thing about the show, if you look back at each heinous stage of our career, it’s nice to have it depicted but not in a shiny way. Like, there are a lot of actively dangerous situations that you’re in, you know, as comics. So it’s definitely nice that you can say it without it being cleaned up. And we say horrible, despicable things to each other all the time. So it’s good to see what it actually is.
Jamie: HBO’s been really great about making sure that we just get as inside baseball as possible, which is a funny thing for a network to encourage. But they see it as, oh, the more specific you can be, the more relatable it actually is. So it’s been really cool to me, like no, go deeper. You know, what did it really feel like when that thing happened? And, like, what actually happened? I feel like we’re encouraged to just hone it as much as we can versus like Rachel was saying, polish it up, make it shiny. You’re never going to get that version on this show.
Rachel: Yeah, whenever you see stand-up usually on TV it’s a complete farce. Everything’s made to be quite lovely. It really isn’t lovely. They’ll send any sex offender to get us from the airport. So it’s crazy, very, like, messy, filthy things are happening.
Jamie: With Marvelous Mrs. Maisel, it’s so funny because it’s a period piece, but they do such a good job of somehow capturing the accuracy of, like, how hard–it’s so hard. And you really feel it when you watch that show. And it’s crazy because it’s about, like, 1959. I’m not talking about the look or the clothes or anything like that. That’s not necessarily similar to what we experience now, but there is an emotional accuracy to that show. There’s, like, a humiliation level and just, like, kind of grappling with who you are that’s very, very visceral and real, I think.
Rachel: It’s true. When you think about when you started and it’s like I can’t believe we did that to ourselves. When you’re going through it, you don’t realize it.
Jamie: This is my normal. And then you look back and you’re like, oh, I should have PTSD.
Rachel: Yeah, what would my psyche be like if I hadn’t done these strangely deranged and abusive things throughout my twenties?
Question: There are so many shows about stand-up. Does it take you out of a show if the stand-up isn’t accurate? Do you prefer accuracy over just being funny?
Jamie: Anything on TV, I think the number one goal is make sure it’s funny. But I think that, with Crashing, part of the promise of what we’re delivering is the accuracy as well because it’s technically something that very few people know about.
Zach: I don’t do stand-up. I learned all this from watching Crashing.
Rachel: That’s how I felt about Don’t Think Twice, although I’ve heard other–not you–but I’ve heard other improvisers say, like, loved the movie, wasn’t the most accurate, which is you have to move the story forward.
Zach: The movie Don’t Think Twice is, like, an improv movie and I came up through improv. And it’s not, like, a 100 percent accurate, but it is cool seeing it depicted because most people don’t get to see that. So, for me, that’s almost more important. It’s just like it’s fun watching what you went through being depicted for a broader audience.
Jamie: I think any other type of show, funny over accuracy, absolutely. But when you’re touching on a subject that has been touched upon in so many other shows, I think accuracy is maybe the only thing that’s going to fully set you apart, probably.
Rachel: [Crashing] does service, like, in terms of the actual stages of what you go through. I mean it’s really educating anybody that doesn’t know what happens. My own girlfriends ask me questions about it. Like, did you do that thing? Did you do that? Like, you can talk about barking but nobody knows what the hell you’re referring to. And then you actually see it. And they’re like, did you go through that specific stage of debilitating humiliation?
Question: Have all of you barked on street corners to attract audiences to clubs to earn time on stage early in your career?
Jamie: I never barked.
Zach: I never barked either. Maybe one day.
Jamie: I did bringers, which is sort of barking lite.
Rachel: I did more of bringers too.
Jamie: That was my very first show I ever did. I was a bringer for Carolines on Broadway. And I think they told me I had to bring–there was one show–I don’t remember what club it was–they literally said, can you bring 20 people?
Rachel: It was Carolines, I think.
Jamie: I was like, do you know 20 people? I don’t. I did it.
Rachel: Me too. I went into bars.
Jamie: Oh my god! That’s genius. My whole family happened to be in town. So that was, like, 10. And I found, like, the other 10, just a random…
Rachel: And you’d be so nervous. I have them come and then I can’t even get up because it’s so embarrassing. Yeah, it’s absolutely terrible.
Question: Jamie, can you talk about coming from just writing on the show to now also starring in it?
Jamie: I don’t know if writing on it really helped so much with the acting. I think the fact that I went through pursuing stand-up in New York, I think that was the most valuable tool, just to be like, oh, I went through this. So it was kind of cathartic to depict it on TV. But there was a little bit of, like, well, I am familiar with how this character has come to be in the writer’s room even though we wrote it kind of being like–you know, we took elements from a bunch of different things and sort of piled them into Ali. She’s a Frankenstein, but like an arm of one person and, like, another person’s nose. It literally is all these different archetypes kind of shoved into one character. So yeah, I guess then, when I got the role and auditioned for the role, I was like, I feel very confident that all I can do is try to bring my own experience to this because there are a lot of people auditioning and everything was truly out of my control. So I just kind of went in with that attitude of, like, what can I bring to this?
Question: Ali wasn’t written with you specifically in mind?
Jamie: No, very much the opposite. There was a moment very early on when I had heard that there was a role. And I was like, that sounds amazing. But there was no part of me that was like, okay, well I’m already in the room, so maybe I have an advantage here. It was the opposite in that I think, when you’re in a writer’s room, you’re kind of like the last person anyone thinks of, which is kind of weird because it’s like you’re right there. But it’s actually very counter-intuitive. It’s not helpful because I think a lot of times–and I can’t speak for every writer’s room; I’m not even speaking about my own writer’s room–it’s just you think, well, I’m here, so choose me. And it’s like, that’s not how it works. They’re going to see everybody. It’s not even just the producers, or it’s not even just Pete. It’s like there are people at Judd’s [Apatow] level and then there are the people at HBO. There’s so many people you have to get through. So you’re never going to, like, circumvent the casting process, at least not at my level. There’s no way around that.
Question: Were there experiences from Pete Holmes’ time starting out that the show held back?
Jamie: I feel like he’s been very open book about wanting to mine his own experiences. I think that’s kind of how the show, is we start with, like, remember that one time. And then we start with, like, the nugget of truth and then kind of like figure out a way to work it into the narratives. And so I think that is probably why the show is accurate, because, for the most part, everything stemmed from a little moment of truth.
Question: What is your process for writing comedy? Do you tend to write linearly, work backwards, or does it vary?
Rachel: For me, I usually have a deadline or some sort, and I panic. So people always ask you how you write and I’m like, I don’t. I just wait until it looks like I’ll be in trouble and then I start writing.
Jamie: Well, John Mulaney–I don’t want to completely misquote him–but someone, maybe it was Pete, told me he does something similar. The deadline is what forces it out of you.
Rachel: Yeah, usually, like the last special I did, I didn’t show them the tape first. I’m afraid I’m making a fool of myself. And usually then I fantasize about there being some kind of a fire or something. I have fire-based fantasies. Oh, maybe there’ll be a little fire in there and I won’t have to perform the special. And then I kind of stay up and write it. But it’s all through panic.
Jamie: There’s also something–I don’t know if you feel this way, but when you have to actively type out your jokes, there’s, like, a real process of self-awareness where you’re like, that’s what that joke is? Like, you get to the point where it’s good to confront your material or something. And it also commits it to memory, and say it, yeah.
Question: What are your dreams for Season 3?
Jamie: Well, I think we’re at a stage where we feel like anything can happen in Season 3. We don’t want Pete to have too much success too fast. So I think that gives us a really fun timeline to play with because there really are a lot more milestones to be had before he, like, you know, makes it big, as they say in the biz.
Rachel: I’d like to see shit hit the fan.
Jamie: I mean that’s always a great option for every show.
Rachel: This season is really wild. This season is covered in sin already. I’d like to see even more sin the next season. But Pete definitely goes rogue in this season. He goes rogue.
Jamie: It’s Pete unleashed.
Crashing Season 2 premieres January 14 on HBO.