Jessica Williams, Leading Lady


At just 22 years old, fresh from college in Long Beach, California, Jessica Williams became the youngest reporter on the satirical news program The Daily Show. A quick-witted young woman with a topical and cutting sense of humor, she soon gained a strong fandom, which continues to follow her five years later. Although she resigned from the show in 2016, things have never been busier for the rising comedy star.  This week she stars in the new Netflix film The Incredible Jessica James, an indie comedy about an aspiring playwright dealing with a recent breakup.

When we meet Williams in Manhattan on a rainy Monday morning, she confides in us how long it took for her to get ready. In 2 Dope Queens, her podcast with Phoebe Robinson, Williams often brings up the politics of women’s beauty regimens. It is not the only subject she demystifies in her comedy; whether it’s the aggravation of catcalling on The Daily Show, caring for a single mother in People Places Things, or simply exuding female confidence in Jessica James, Williams never sugar-coats how it feels to be a young woman in these perception-obsessed times.

Although humor is currently her primary vehicle, it’s not hard to imagine Williams venturing into more serious territory, especially given her admiration for filmmaker and fellow Californian Ava DuVernay. 

ZUZANNA CZEMIER: How did you and James Strouse first meet?

JESSICA WILLIAMS: We met because he wanted me to do the movie People Places Things. We met at this coffee shop right next to The Daily Show and we really got along, so I signed up to do that movie. In that movie I was a supporting character and Jim was really complementary. He was like, “I cannot wait until someone writes you your own movie.” Then he texted or emailed me and said, “I want to write a movie for you.” We met up a bunch of times and talked about this character and the story and he kept sending me drafts. We moved forward and shot it really quickly.

CZEMIER: Seeing you on The Daily Show and listening to 2 Dope Queens, it seems to me that there is a lot of you in the character of Jessica James. How did it feel to have this part written especially for you? Did you contribute a lot to writing her dialogue?

WILLIAMS: When Jim approached me it felt really nice, just because he’s a very sweet white guy. I said, “Thank you. Please, I appreciate it.” I felt really grateful. I adore him; I think he has such a good sensibility in general. We met a lot, because he was very respectful and wanted to make sure that the dialogue felt accurate and something that somebody my age would say. I come from a comedy background, so he allowed me and the other actors to improvise often. A lot of the stuff we ended up not using, but many things we all improvised actually made it into the movie. That was really exciting. I was involved with the movie from concept to creation, so I was able to chime in and say things like, “Can we change this line into this?” Lines like, “I would rather have my period non-stop for a thousand years than continue this part of the conversation,” that was me improvising in the moment. It was nice that Jim created a set where that was alive.

CZEMIER: You studied creative writing and film at university. Now you’ve worked in film, TV, and theater, and you’ve done a podcast. Was film initially what you wanted to do and did it seem like a feasible goal at the time?

WILLIAMS: I wanted to do something that had to do with film. I wanted to do screenwriting. That’s what I went to school for, but my major was overfilled, and when I got The Daily Show, I was a semester away from officially starting my major, so I never started that in particular. But I always wanted to work in film and TV, just because it seems like these are great formats for reaching people.

CZEMIER: Could you talk a little bit about the differences between performing for a live audience and in front of the camera?

WILLIAMS: It’s so different. There’s such an adrenaline rush for me on stage and having all these people look at you. There’s an adrenaline rush from not having things written down too. The risk is that we are trying to discover stuff on stage about each other, whereas with acting in front of the camera, at least for me, it is about being calm and being present, being in tune with and intimate with whatever the relationship is that you’re conveying on screen and not being so big. With live shows, it’s a completely different beast. Even with The Daily Show, we performed in front of a live audience with three cameras there. You’re collaborating with someone else always; you really just get one shot. When I got to the set of Jessica James, Jim was like, “Great. Do you want to do that again?” and I’m grabbing his shoulders, “Oh my gosh I can do it again? Holy shit, this is such luxury!” It was really different in that I had so many takes, whereas with The Daily Show, and with the live performances that I’m used to, you get one shot. I enjoy both, but I know after I do a live show I’m exhausted. I’m ready to sit down and chill.

CZEMIER: Do you think being on the spot like that has shaped your comedy?

WILLIAMS: Yes. It’s a really nice way to cut your teeth, doing live shows. It’s like going to the gym, because you do have to think fast. You are constantly under the threat of people not laughing. Instead of getting hit, people could just not laugh, so you really are trying to mine quickly for the funniest thing you could say in that moment. I do think that that translates on set too; your brain is automatically trained to ask, “What’s the funniest thing? What’s the clearer joke to get there? Is this truthful?” You really have to mine quickly for things to be funny.

CZEMIER: I imagine that takes a different kind of preparation, or do you just go in cold?

WILLIAMS: We just go in. The main thing that we want to do, if it’s a live show, is to try and be ourselves wherever we are. When we’re not being truthful or not being ourselves, that’s when it’s not good. So there’s really no prep. The best thing we can do, at least for me, is to be excited about the show and excited about playing with the other person.

CZEMIER: You and Phoebe Robinson are really open and easygoing 2 Dope Queens. Do you ever catch yourself thinking that you might have overshared?

WILLIAMS: Oh yeah. Sometimes I wake up in the middle of the night with night sweats being like, “What did I say at the show tonight?!” But I really try to be respectful of my actual personal relationships and keep them at arm’s length. Sometimes we’ll get the cut and be like, “Hmm, can we not put that in there?” The both of us will think, let’s dial this back. Watching the shows, sometimes I wish I elaborated in this or that way. We really have to make sure we’re not selling out everybody that we know and love.

CZEMIER: Has it ever happened that someone gave you a funny look on the street or are the reactions always positive?

WILLIAMS: No, everybody is always really nice. When I wake up in night sweats that’s what I’m thinking about: what if someone grabs me from my past and says, “I heard you drag me to filth on your podcast.” [laughs] Sorry man, you shouldn’t have been a douche.