Crashing Season 2: Jamie Lee On Going From Writer To Co-Star

There’s a scene in Crashing, which returned to HBO for its second season this week, where Pete Holmes tries to convince John Mulaney to give up his stage time in an effort to help impress a fellow comedian named Ali Reissen. Trying to justify the interaction, Holmes tells a confused Mulaney that his dad once told him “if you want something you need to ask for it.” To which Mulaney responds, “Your dad sounds like an idiot.”

Holmes was overstepping his boundaries, as he consistently does on the show, and Ali, played by comedian Jamie Lee, rightfully scolds the wannabe comic for interfering. In a weird way, the truism from Pete’s dad sets up the dynamic between Pete and Ali, a budding relationship that gives Pete a new outlook on his personal and professional life.

So who better to step into the role of Ali than someone who’s had comedic chemistry with Holmes for nearly a decade? Lee and Holmes wrote and acted in a web series called Kid Farm, which was picked up as a digital series by Comedy Central in 2011. While their standup careers blossomed, their working relationship continued as Lee wrote for The Pete Holmes Show, a talk show hybrid that ran for two seasons on TBS. Since then, Lee’s written a comedic book called Weddiculous and returned to work with Holmes as a writer on Crashing. 

Acting was a passion for Lee, but she had yet to have a breakthrough TV role. Though it’s not often people go from the writing room to co-star, Lee had her “if you want something you need to ask for it” moment and auditioned for the part of Ali. She got it, and in Crashing, she’s reliving the scenes that helped shape her career, the successes, the bombs, and all the unglamourous stuff in between that undiscovered comics have to go through.

Ahead of the Crashing season 2 premiere, we sat down with Lee to discuss how Ali’s gift to Pete is a comic compass, what the show gets right about the New York comedy scene, and opening up on stage. 

Den of Geek: So you were a writer last season now you’re a co-star. How did that come about?

Jamie Lee: Yeah, well I auditioned. I in no way thought that being a writer would be a foray into being an actor in the show. Just typically, I think there are a lot of writers where they’re like, “Oh, I hope that happens,” but it doesn’t usually. So, the fact that it worked out that way was pretty shocking in a really wonderful, dreamy way. 

I’ve always wanted to act and I’ve been auditioning for a long time. I was on Girl Code, so I’ve done on camera. Mostly Girl Code and just doing stand up on TV, but I’ve always wanted to act and I studied theater in school and then when I first started out in stand up, I thought it was really not okay to want to admit that you wanted to act. Like, I always thought that’s just admitting that you’re not a standup purist, you know?

So I was like oh, I can’t ever tell anyone. I have to like keep it on the DL. Because it also sounds douchey or like, “I’m an actor.” Like, that’s just not … I just felt like it was not okay to say, and then when I moved to LA I realized that just in a kind of more enlightened LA way, you should just say the things you want because that’s the first step in making them happen. I actually believe that’s true. I think that if you just kind of like declare your wants, it in some way comes back to you just because you’re admitting it to yourself.

The growing alt-comedy and podcast scenes also factor into the show. With so many diverse ways to get into comedy right now, do younger comedians still view standup as the pinnacle? 

I think the cool thing is that I think everybody is starting to consume comedy whereas before I feel like it was kind of like almost like liking an indie band. It was like, “Oh, have you heard of so and so?” And now it’s shocking the amount of people who know my level of comedians. It used to just be like you know the headliners who sell at stadiums, but now it’s like oh, people are actually taking interest in comedians, not just for their comedy, but also for their personalities because they’re just hearing them on podcasts. You connect so much deeper with people on a podcast because you’re like, “Oh, it’s like I feel like I know that person because I just heard them tell their life story for the last hour and a half or whatever.” So, I think it’s actually a really great time to get into comedy. It feels a lot less pipe dream-y.

Your character, Ali, tells Pete that it’s kind of hard to get into the personal stuff on stage and she’s working her way up to that. In real life, does being on podcasts where you’re able let go and have these more intimate conversations then make it easier to then go up on stage and do it?

I think so. It takes a certain type of personality to expose your personality on a podcast so intimately and you know that people are hanging on every word because they’re just being fed through their ear buds. There’s just such an intimacy in that experience. I’ve heard people stumble upon bits just by doing their podcast.

There’s an episode later in the season where Ali brings Pete to an eclectic mix of shows around the city. With all that going on in New York, does that kill some of the romance of being a road comedian since you can do multiple sets in front of diverse crowds in one night?

That’s a great observation because I think that there is a lot of grind that takes place just in one night in New York City that is just as harrowing as being on the road, like the romance of all the solitude. It can be a pretty solo pursuit to just bounce around from show to show in one night. I mean, you’re very focused and maybe you’ll go when you’re starting out in stand up. You’ll go with a friend to a show, but for the most part you’re just kind of like on your own just taking the train all over the place. There’s definitely that sort of hitting the open road feel just in pursuing stand up in New York.

How important is that repetition? To be able to do a couple of shows in a night?

You know, it’s interesting that you ask that because I think about it a lot. It felt, at the time when I was starting out in standup, like if I didn’t get up a bunch I would die. It felt like I would be rusty, I would forget how to do stand up. If I didn’t do stand up for one night, I would beat myself up so hard. If I took a night to go to the movies with a friend, I felt horrible. 

Looking back, I don’t know if that’s because I was on to something or if because I’m the most anxious person alive. I genuinely don’t know and I wonder, because I think sometimes if you get up on stage a bunch, you almost become too comfortable and then the good thing about that is everyone wants to be comfortable. It’s comfort. But then the other part of that is that you get really okay with bombing because you’re like, “I’ve done it 100 times. This happens all the time.”

And you can go do it at the next club.

Yeah, and you’re like, “Oh, maybe I’m actually not challenging myself as much as I thought I was.” I think about that a lot. I’m like, was I actually doing myself a disservice? I don’t know.

What does Crashing best capture about the New York comedy scene?

It captures that there’s kind of like two scenes in a way. There’s the club scene and then there’s the alt scene, and now there’s a lot more crossover. Club comics do alt rooms and alt comics do clubs. It’s a lot more blended, but at a time it was pretty separate and I think that we do a good job of showing that you don’t just have to go to a comedy club to see stand up. It’s actually everywhere in the city and outside of the city. It’s all over. I would like schlep to Jersey for shows all the time and they would be in like a sports bar and they literally have to like turn off the TV’s and then there would just be like an amp at the back and people would just like stand there. I mean, that was a show. Sometimes they were the best shows. It’s crazy.

I feel like Pete represents the casual comedy fan stuck in the old way of looking at the industry, but he continues this progression and education through the show.

He becomes more current. I feel like the character of Ali really wakes Pete up and she also pokes holes in his façade in a way. I think that that’s what’s fun about their dynamic is she doesn’t buy his nice guy routine and I think that that’ll be refreshing for viewers as well because I’m sure that they’re picking up on that and I think a lot of times when you watch Pete in a really great way, you’re like screaming at your television. Like, “Oh my God, I can’t believe he said that. Oh my God I can’t believe he did that.” And I think my character’s the person who’s like showcasing that front and center.