On a cool December morning in Los Angeles, comedian, writer, and actor in HBO's Crashing Jamie Lee can't help but be a little distracted. While sitting across from me bundled in a sweater on the patio of Go Get 'Em Tiger, a bustling Hollywood coffee shop, she spots several familiar faces. The first is her husband, fellow comedian Dan Black, who's walking their adorable labradoodle Dennis; the pair joins our small table for a bit. A few minutes later, Lee waves over Reggie Watts, the band leader of The Late Late Show With James Corden (writer: Eliza Skinner), who stops by for a quick chat. It's a series of serendipitous moments that feel like a real life, L.A. version of Crashing, which follows creator and star Pete Holmes as he runs into fellow comedians in comedy clubs and on the streets of New York City.
It’s fitting, then, that Season 2 will be giving Lee a properly happenstance Crashing entrance. We first encounter Lee's character Ali, a hardworking and independent comedian, when Pete talks to her outside of a comedy club in New York City. The two strike up a friendship, which blossoms into a romantic relationship, and the season spends a significant amount of time exploring the experience of trying to make it as a stand-up through Ali’s eyes. It’s a refreshing change of perspective from Crashing's first season, which, though it did feature a handful of brilliant female guest stars, focused solely on the point of view of Pete (Holmes’ semi-autobiographical character) as he struggled to accept his split from wife Jessica (Lauren Lapkus) and began doing stand-up comedy in New York City.
Incorporating Ali’s experience into the show is a welcome shift that broadens the perspective of the series beyond its origins as a show about a straight white male comic. And though Pete and Ali do date, unlike some female love interests on other comedian-auteur TV series like FX's Louie or Netflix's Master of None, Crashing doesn’t treat Ali as merely a “girlfriend” character, but rather as a well-rounded, career-oriented woman who's Pete's equal. As a focused, hard-working comedian with a strong voice, Ali contrasts nicely to the mild-mannered Pete, who often finds himself on meandering detours and dealing with random misunderstandings in several episodes. It's clear that Pete admires Ali for having her sh*t together, and that's particularly on display in one episode, when Pete devotes an entire night to helping Ali achieve an important stand-up goal as she hustles to several shows. Clearly, Pete is attracted to Ali because of — not in spite of — her drive, which is something that's still unfortunately rare to see on TV.
As a writer on both seasons of Crashing, Lee helped ensure that her character’s perspective felt authentic in the script, and she had plenty of experiences of her own to draw on. In the first episode of Season 2, Ali asks to speak to a comedy club's manager and Pete asks her, "Do you have a complaint?" not even thinking that she too is a comedian. Lee says that was a very common experience for her as an up-and-coming stand-up at comedy clubs. "Probably the biggest thing that happens most frequently is that people are really surprised you're on the lineup," she recalls. "I'll go to a club and I'll walk up, and I'll be like, 'Oh, I'm on the show.' And they look at me shocked: 'Oh, you're performing?'"
Later in that episode, Pete introduces Ali to comedy club manager Jason, who doesn't even glance at her and only speaks to Pete. "It's not influenced by a specific experience, but it 100 percent feels very real," Lee says of the scene. "Unfortunately, a lot of times I'll notice if I'm in a group setting, guys will just speak to guys. Then the girls are kind of the sidecar."
But while Lee did incorporate real experiences from her life as a stand-up into the show, and even wrote some of her old material into Ali's stand-up scenes, she's quick to note that Ali isn't a strictly autobiographical character. "I think that Ali is an amalgamation of young, hungry, female stand-ups in the New York comedy scene," she says. And although she had Holmes did date roughly 10 years ago, Ali and Pete's romance isn't at all like what happened between her and Holmes. "I think the relationship between Pete and Ali is very different and very separate from my relationship with Pete, which was very fun," Lee says. "But we very quickly realized that we were better as friends. Then after that, we realized that we were really good at working together."
That's led to Lee becoming a writer on Crashing and appearing as an actor on the show. On January 19, she'll make strides in her real-life stand-up career, too, by releasing her first stand-up album. And while there’s a ways to go before the boys club mentality of the stand-up scene completely disappears, Lee says she no longer feels like she has to focus on curbing her femininity and the amount of personal stories she tells on stage. "I think it's more in the zeitgeist to embrace [being a woman onstage] now," she says when asked about how she tackles the challenges that come with being a female comedian in this political moment. "I think it's a really great time to be a girl in comedy. I think that the industry is really looking for more and more and more of us. So keep your head up and just work really hard."
In fact, Lee's role on Crashing came to be because of her own desire to embrace the zeitgeist and help increase diversity and female representation in comedy. Before getting the on-screen role of Ali, Lee created another smaller female role in the show’s writers room, hoping to play the role and add another female voice to the show. “I kind of took it into my own hands to write a smaller part for myself on the show just in case something larger didn't happen,” she says. “I was like, ‘Well, maybe I could at least be in one scene or something.’”
Fortunately, Lee won the role of Ali, and the addition of a female comedian main character has changed Crashing’s Season 2 dynamic for the better. It's something that Lee is proud of. "It was very exciting. I think that my mission in everything that I touch, Crashing and otherwise, is always to get more women and more diversity on shows," she says. "It's always my thing. Almost obsessively so. So it felt like, 'Oh, we're just getting a step closer to that on [Crashing].'" Now more than ever, Lee understands that women's stories need to be told, especially in comedy — and, like Ali, she's driven to make it happen.
This story was created in support of Bustle's 2018 Awards Season pledge. Read more here.