The comedian-writer stars as Ali Reissen in the second season of HBO's 'Crashing,' which premieres on Jan. 14.
You would think Jamie Lee earning the role of Ali Reissen on Crashing would’ve been a no-brainer.
After all, Lee, a Texas native, cut her teeth in New York City’s comedy scene. She also dated Pete Holmes, the stand-up comedian who created the semi-autobiographical HBO series, for about 11 months almost a decade ago. While Lee sees herself in Ali -- a Boston comedian who bounces around alt-comedy rooms, a notion the 34-year-old comedian remembers from her early days -- Lee is not actually Ali -- and that’s an important distinction.
“I think that the determination and the sort of unstoppability, that is very much me and also the character, [but] Ali is a lot more confident and knows her own voice and believes in everything that she's saying and stands by her material in a really self-assured way,” Lee tells ET. “When I was starting out, I was a lot more, 'Is this right? Am I doing this right?' -- seeking approval and trying to find my voice. Ali is someone who's kind of ahead of the curve in that way.”
Ali, who will be a recurring character in the second season, also brings a new side out of Pete over a series of episodes that show him questioning his faith while finding his voice.
“In contrast to Pete, who is sort of sweet and naive and trying to find herself, Ali very much knows herself -- or thinks she does --- so it's a very fun contrast to have someone who's kind of not sure of themselves paired with a person who is, like, 'Let me tell you who you are,’” Lee says.
As perfect as she is for the role, Lee had to fight to earn it. A writer on Crashing, Lee auditioned for the role, which Holmes initially didn’t think was right for her (and, it should be noted, is not based on their relationship). But when auditions opened up, she tried her hand alongside 100 other women.
“I was in no way like, 'It's going to be me!' The chances of that happening are so slim,” she admits. “I already had a smaller part that I had written into the episode -- and I'd still have to audition for that! No role is ever handed to you. If you get to a celebrity level, of course it is, but when you're more of an up-and-comer, that's just not reality.”
After earning the role, the Weddiculous author was plagued by sexist assumptions that she got the part because of her history with Holmes rather than on her own accord, which she wrote about at length in a recent Lenny Letter.
“I can't control what is said. That's kind of where I landed with that. You can only control what you can control,” she tells ET. “The thing we're capturing in the show is that it is very natural when you're starting out in comedy to want to date comedians, because you've finally found people who not only get you as a person, but they understand the lifestyle and the end game. A lot of people don't get it, and it's a lot of explaining your dreams to people who look at you with a blank expression, and you don't have to do that with other comedians because they're in it too.”
“The cool thing about Pete and I is, even though we dated and that was that, it's like that chapter ending just meant the beginning of a friendship and a work partnership that's really valuable,” she adds. “So, in that regard, I'm just really happy that it worked out that way.”
In fact, it’s because they had a working relationship that Lee and Holmes reached a place where they can be around each other so frequently. While dating, they created a pilot called Kid Farm, which got picked up as a digital series after they split.
“We were sort of put into a situation where we had to work together, and it forced us to shove our baggage together very quickly and focus on comedy, and I think that was a really big gift to our friendship starting out, because our friendship started out in a business context and then grew back into a friendship,” she explains. “It kind of happened in an organic, best-case scenario way. It also helps that he loves my husband [Dan Black]. I love his wife [Valerie Chaney]. He's kind of just family to me now.”
That being said, she’s got some sound advice for people who are stuck working with exes: “If you feel like you're not compromising your sanity and who you are to work with them, then continue doing it, because self-care is the most important thing.”
Stand-up comedy is a tough business, regardless of your gender, but there’s a well-known, unfortunate extra hurdle for women, whether they’re starting out or writing for an HBO show. Playing Ali has allowed Lee to reflect on her early days in comedy, which she’s realized were “especially challenging” when looking back at her roots with fellow comedians like Aparna Nancherla.
“I think the thing I would tell my younger self is don't be afraid to take up space and don't be afraid to fail. It doesn't mean that you're a failure, because failing is the only way to get good,” she mused. “It is a boys' club and I felt a lot of pressure and intimidation, and I wish that I had just kind of not cared as much.”
Women are finally taking up that space, speaking loudly amid Hollywood’s recent sexual misconduct scandals, as evidenced by last week’s Golden Globe Awards and the Time’s Up initiative. For her part, Lee says she’s seen a shift and is “optimistic.”
“Oprah [Winfrey] was a huge part of it, but it was all of it. It was so much. It wasn't just like, 'Oh, we're all wearing black.' No, literally all of the content is about that,” the Girl Code alum said of how she felt watching the awards show on Jan. 7. “So many women won, and then when it was only men nominated for director, someone said something. There was a real fearlessness in the air that I think went a lot deeper and a lot further than the concept of an awards show for celebrities could ever go, and I think that was really shocking and surprising. It was so good.”
One of the big winners of the Globes was The Marvelous Mrs. Maisel, which Lee is “absolutely obsessed” with. “[Midge Maisel] is a comedian in the late 1950s, yet there are so many similarities to her experience that I feel,” she gushed. “It's not obvious. I can't point to a specific scene or even a moment in the show -- it's just little looks and micro-moments where I'm like, ‘Yes, that is so spot on.’ It’s really healing to watch.”
Lee has plenty more comedy on her plate, so the hit Amazon show seems like perfect inspiration. Not only is she writing and acting in Crashing, her first stand-up album, I Mean, drops Jan. 19, and she’s gearing up for a special featuring new material later this year. The acting bug has also bitten her hard, so while she says she’ll “never abandon” stand-up, she is setting her sights on more acting roles, hopefully in movies.
“The thing I like most about acting on the show is just getting to act, because I realized how much I love acting and how important it is to me,” she said of this upcoming season of Crashing, which is also executive produced by both Holmes and Judd Apatow. “I used to think it was kind of embarrassing to admit you wanted to act. It just sounded so pipe-dreamy, but the fact that I actually get to do it professionally is not pipe-dreamy now -- it's just really dreamy.”
The second season of Crashing premieres on HBO on Jan. 14 at 10:30 p.m. ET/PT.
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