Recently heralded by Time as one of the 12 new faces of black leadership, Jessica R. Williams joined the The Daily Show in the winter of 2012 — making her the youngest correspondent in show’s history at 22. Even if you’re not an ardent follower of the Comedy Central program, chances are you’ve seen Williams’s uproarious work around the Internet. From educating white people on the complexities of African-American hairstyles to exploring the catcalling epidemic, her pointed, hilarious segments are frequently the highlight of the show. In fact, her work with Jon Stewart and company is what attracted the attention of James C. Strouse, the writer/director of People, Places, Things, in which Williams stars as a budding cartoonist attempting to set up her college professor with her single mother.
During this year’s Sundance Film Festival, Williams — tall and radiant— sat down with Playboy to wax comedic and profound on everything under the sun. Opening up about her thespian desires, people paying her compliments, and our Lucky 7 questions, it’s clear the charming, quick-witted Williams has a promising career ahead of her.
I’m going to ask you incredibly personal questions.
Mm-hmm. Thank you, I like this.
When you got the script for People, Places, Things, did you know this was something you had to do?
I didn’t feel like I had to do it, but I wanted to. I really liked it. What I liked about it was that it was funny on the page, and I got to work with Jemaine [Clement]. The character was very well thought-out, and that’s what I was most excited about.
Are you into comic books?
Comic books? Yeah. You know, nobody’s asked me a comic book question yet, which is very interesting. I’m also into graphic novels and I liked the idea of playing somebody like this.
I’m surprised no one’s asked you a comic book question.
It’s really weird.
What are they asking you about?
You’re great. You’re doing great. [Laughs.] I love this.
Your character here is reminiscent of the role you play on The Daily Show.
Yeah, because Jim kind of approached me for the film because he liked The Daily Show. It wasn’t like it was a huge stretch. I guess I was playing myself, which was nice. And I think that comes out in The Daily Show too.
So you are playing yourself.
Yeah, a lot of us are playing heightened versions of ourselves on that show.
Is acting what you want to do?
Definitely. I’ve always wanted to be an actor and I discovered improv and sketch and I really liked it.
There’s a style and technique you bring to The Daily Show that really shows you have acting abilities.
Oh, thank you. I appreciate that.
Do you hate people who pay you compliments?
Yes. Do you?
They just don’t really know me.
Yeah. You don’t know me. You don’t know how evil I am inside.
Are you shitty inside? Is that what’s going on?
[Laughs.] Yeah. No, I don’t think I’m shitty. I think “shitty” is so relative. I think “shitty” is like, Hitler is shitty. So I think being shitty is such an extreme. “Not tight” is probably how I would describe myself.
So you’re not a perfect human being?
I’m not. I would love to be. It’s the thing that gives me the most anxiety. It seems kind of cool. You know what it is? It’s super-intangible and that’s why I like it. You know, like, a donkey with a fuckin’ carrot. Like there’s a carrot on the stick or something and the donkey’s trying to get the carrot. You’re not going to get the carrot. You keep trying; you keep trying to get it.
I could take a break from trying.
No. You’re hungry for something. I don’t know man; this is the most philosophical interview I’ve ever had.
What was your first exposure to Playboy?
I was never really exposed to Playboy. I didn’t have an older brother who snagged it. You know what? I would always go into the 7-Eleven and see Playboy but it would always have the plastic wrapper over it, where it would cover the ta-tas and the na-nas, and you’d just see the face. I’d be like, “Oh, that’s Cosmo,” and then, “Oh, that’s a magazine with a plastic bag over it.” I couldn’t buy one though. I wouldn’t be able to get away with that. My parents were helicopter parents. Always circulating. That’s fine; I turned out very moralistic, I guess. But I like them more as I get older.
What movies scared you the most when you were a kid?
I love scary movies. I like love-hate them. Probably The Exorcist. That was fucked up. Paranormal Activity kind of freaked me out too, the first couple. The Grudge freaked me out; The Ring. Those two freaked me out.
What is your pop culture blind spot?
Classic rock. Like, Zeppelin. I couldn’t tell you about Pink Floyd or Zeppelin or anything like that. A lot of my white male friends say, “It’s fine; I grew up with it. It’s fine, but you’re not missing anything.” I go, “Thank you.” I could talk to you about Motown, because that’s what my parents listened to — you know what I mean? But that and anything that has to do with economics, like the way the economy works.
If you ended up on death row — which, hopefully you don’t — what would your last meal be?
Definitely breakfast. Grits. I love breakfast. Grits, bacon, eggs, pancakes. Yeah, so much bacon. So much bacon. Eggs; scrambled eggs. And then maybe pizza on the side. I love pizza, so it’d be breakfast and pizza.
What was your first car?
My mom’s Camry. Then I got a PT Cruiser. It’s a convertible. You’ve got to start with something shitty like an old Camry, and then work your way to a dad car, like my convertible PT Cruiser.
What was the first song you knew all the words to?
It was a song called “Freak Me”; I think it’s by Silk. I knew every word. My mom had to be like, “You can’t sing ‘Freak Me’.” Because there was a very big “Freak Me” culture in R&B in the early ‘90s. Everyone wanted to get freaked for a while. Adina Howard wanted to get freaked. There was a big freak culture, so I knew most of the freak songs.
What was your favorite mistake?
I’m so embarrassed. I told a teacher of mine that she should keep her legs closed because she was having a bunch of kids, and I wanted to be her favorite, and I was jealous that she was having kids. That’s why I said, “Why don’t you keep your legs closed?” And I was maybe, five? That was a huge mistake. I don’t know; it just came out of nowhere, too. But that was when I was like, “What was that?” I think that was my first instance of being witty or saying a joke or something. But it was very hurtful. So I definitely wasn’t her favorite. I was jealous. It was my daycare teacher. It was so devastating, and it caught me off-guard. It broke up her and my relationship, obviously, because I used to be her favorite, and it ruined that. We never were the same.
Founder of Movie Mezzanine, Sam Fragoso is a San Francisco-based journalist whose work has appeared in Interview Magazine, The Daily Beast, Forbes, RogerEbert.com and The Week. You can follow him on Twitter @SamFragoso.