About a month ago, I hopped on a phone call with Pete Holmes to discuss the third season of his semi-autobiographical HBO comedy series Crashing. He was at the Crashing offices in New York City, taking a quick break from working on the show to chat for a bit. He was just as I’d hoped — super nice and very funny. We talked about his latest comedy special Pete Holmes: Dirty Clean for a bit and then we got down to business and I asked him some questions about season 3 of Crashing, which premieres this Sunday, January 20th.
AiPT!: At the end of season 2, you had the roast battle, you broke up with Ali, and it ends up with you doing a college show. To be honest, I thought season 1 was decent but season 2 absolutely blew me away — I feel like Pete had this great arc where he was trying to find himself all season and he accomplished that by the end of it. What’s in store for season 3?
PH: First of all, I totally understand. That’s been my experience with a lot of shows I watch. I’m not just saying this — if that was your experience with season 1 and then season 2, then I think you’ll be very happy with season 3 because it continues upon what season two started. What I think happens is the writers, Judd, all of us get better at making the show. We’re all sort of discovering it ourselves while making the first season. Season 2 you find your groove. And I really feel like season 3 expands and extends that groove.
Pete quickly sidebars to tell me something funny and then goes on to spill some details about season three.
PH: It’s about two main things — one is a new relationship. Pete, up until this point, has only dated from two bubble-like dating pools. One is the Christian world, and one is the comedy world. In the third season, he meets someone that’s out in the wild. And that’s what happened in my real life experience. I was married, then I dated a comedian, and then I dated someone who was neither of those things. It was really exciting, intoxicating, and interesting. To date this eclectic, eccentric, sex positive, free thinking, little bit dangerous, little bit kooky woman that doesn’t really fit into either of Pete’s bubbles…to see how that works and what it’s like when they meet his parents (one of Pete’s favorite episodes), what it’s like when she meets the comedy world, and her jealousy towards Ali…it’s a really fun tension to play with. My character realizes he’s really good at the religious market. So he gets an opportunity to do Jewish shows, he gets to do a Christian tour, and he needs to figure out, similar to season 2, is this who I am? I can certainly get paid, I’m doing better than I’ve ever done, and I’m performing in better circumstances. We juxtapose that with going on the road at regular comedy clubs and regular colleges — regular as in not Christian. And then we see what it’s like once Pete starts finding success. And this is one of those things in show business — when it’s not the success you envisioned, you have to make those hard choices as to what are you going to sell of yourself to maintain it and have a livelihood. So those are the two main things this season.
AiPT!: What you were saying about the writers room gelling after a first season of “finding yourselves” together — I find that with comedies that’s typically the case (The Office and Parks and Recreation both come to mind). Season 1 sets the framework, and then all the best stuff comes once everyone is used to working with each other.
PH: Absolutely. This is why the first season of lots of shows have some higher concept. Like there’ll be some wacky time travel element that maybe they don’t use by season 4, but you need to give viewers a reason to watch the first season. It’s too boring to say get to know these people and later it will pay off so you have to give it something interesting. And that’s a little bit what happened with the crashing on different couches element. Not that we abandoned that idea, but it becomes less important the more you get to know Artie, Lief, Jess, Ali, etc. Then it can become more of a character-driven show. Which is where the real fun is. That’s where the real stakes are, and that’s where the juice is. That’s just good show business advice that I’ve received, and that I would now give. If you’re writing a pilot or pitching a show, know that the high concept might fade in volume as you move on, but you should have something that will have people initially interested right off the bat. Even Breaking Bad later in the seasons became this weird father and son dynamic, but at the beginning it was like “A SCIENCE TEACHER MAKES METH!”
We laugh and then pivot to the topic of Artie Lange, one of the most beloved supporting actors on the show.
JC: Will we see more Artie in season 3?
PH: Yes. Artie isn’t in it as much as season 2. Obviously he was going through some struggles, that’s not anything new. We always have to be like “Let’s write this for Artie and really hope that he’s able to do it.” And he was! He was often able to do it. So he’s in it and he’s great.
JC: I hadn’t seen him in anything for a while before Crashing premiered, and I have to say he is such a great piece of the supporting cast. I love whenever he pops up.
PH: I know! He’s very professional. I always tease him that his next book should be called Consummate Professional. When he’s healthy, he shows up and he delivers. He’s a wonderful improvisor, he takes dialogue and he just naturalizes it. He’s fun to write for. I think I can write in his voice pretty well, but then he takes it and he brings it that extra mile, which is why I think people like him. He’s one of the most likable people, I think the whole country that knows him is rooting for him. He’s just wonderful. And season 4…I hope we get it, and if we do he’ll be a part of it.
JC: Season 3 — would you say it’s still primarily in New York or are you going to be all over the place?
PH: When I was picturing it, I was thinking the way that season 2 ended I would imagine that season 3 might entirely be spent on the road. It could be interesting to see Pete just crashing in motels and hotels now. When I pitched that to Judd, one of the things he said because of all his experience with TV (Undeclared, Love, Freaks and Geeks) is you can’t turn your back on the world you established. So while we do explore what it’s like to be on the road and we do explore new characters and all that, you gotta see Lief, and you gotta see Artie, and you gotta see my manager Chicken Wing.
We go on a tangent to discover the origin of Chicken Wing.
PH: We just call him Chicken Wing because in the first scene he’s eating chicken wings and he did it so naturally. It’s literally in the script – it says Chicken Wing (laughs). And he loved it.
Back to the location of season 3…
PH: Judd was sorta nudging us back towards New York. I joke that New York is a little like comedy in that as a city it doesn’t want or need you. Neither does comedy — there’s already enough comedians and there’s already enough people trying to live in Manhattan. So there’s something metaphorically interesting about seeing Pete specifically grinding in New York. That being said, I’m open to the possibility that season 4 could take us to new locations. But we wanted to do another season in New York. Also just selfishly, because we love being in New York.
Season three of Crashing premieres Sunday, January 20th at 10pm ET/PT.