Jul 17, 2017
The Incredible Jessica Williams
Do you ever have the thought, as you binge-watch a TV show, or listen to a song, or see a film, that, really, there’s something familiar about everything? That no matter how creative a melody, line, or surprise ending is, you’ve encountered some variation of it already—and yet, when done right, it feels like something special and new?
That was my experience with the The Incredible Jessica James. On the surface, we’ve seen it before: an indie rom-com set in Brooklyn that includes heartbreak, new love, and a story of personal and professional growth. But despite its familiar infrastructure, it’s fresh, because Jessica Williams—co-host of the wildly popular podcast 2 Dope Queens, and former correspondent on The Daily Show—is the person who fills its 85 minutes. The film’s writer/director, Jim Strouse, said that he had a rare, preternatural confidence that the film would be a success because of it.
“I never had any doubt that she would be absolutely fantastic,” he told me. “I felt that way writing it, and I felt that way making it, and I was never really worried—which is atypical for me. That confidence was less in myself and more in her talent.”
When we spoke, Strouse was on his way back to Brooklyn from a writers’ workshop upstate via the Metro North train, which follows a beautiful tree-lined route along the Hudson River. That night he would be at a screening of Jessica James at BAM, and afterwards alongside Williams at the audience Q&A. He spoke quietly so as not to bother other passengers; I thanked him for talking to me even though he was in transit. “No, it’s my pleasure,” he responded instantly. “I love talking about Jessica.”
After they worked together on Strouse’s 2015 comedy People Places Things, which stars Jemaine Clement as an art professor/graphic novelist (Williams plays one of his students who sets him up with her mother), Strouse was so taken by Williams’ presence on screen that he wrote an entirely new film just so she could star in it. But the root of Strouse’s admiration for Williams preceded that: “[I was] a huge fan of The Daily Show,” he said. “She made something I already loved stronger. I loved the topics that she covered, and the way that she covered them.”
As the youngest correspondent to belong to The Daily Show’s The Best F#@king News Team Ever (she was 22 when she first appeared on the show; she retired four years later), Williams was funny and captivating. Moreover, she was able to step outside of her own experiences and empathize with the people that she talked to, in an honest, relatable way. Once, she interviewed a group of transgender Americans, one of whom had been arrested and jailed in Iowa for eight days because she was carrying spironolactone hydrochloride, a common medication used in hormone therapy for trans women, but did not have a prescription with her. “Ugh,” said Williams. “I thought it was tough being a black woman. But compared to a black transgender woman? I may as well be a white frat dude at a Dave Matthews concert.”
Ever since Strouse had seen her unique brand of raw but compassionate comedy, he’d wanted to cast Williams in one of his films. In People Places Things, he thought Williams would play well comedically off of Jemaine Clement—but it went even better than that. While editing her scenes, he thought, “My god, I can’t wait until she is in a movie where she is in every scene, because she is so fun to watch.”
A beat or two later, he realized he could be the one to make that movie.
Williams herself did not take much convincing. “He reached out like, ‘I have this idea, would you like to meet and talk about what I have so far?’ And I was like, ‘Yes, of course.’” Over the course of a few meetings in Bed-Stuy, Strouse presented Williams with the character he was developing. “He really tried to make it feel […] like this was a whole, living, breathing person.”
Watching the film, I was struck by how often things Williams said as “Jessica James” were not just something any living, breathing person would say; they were straight up Jessica Williams. “I am an executive producer of the movie as well, so I had a lot of creative input and say in what happened with the film, and we really wanted to make sure this dialogue felt natural,” Williams said. Strouse also encouraged a lot of improvisation; Williams and her co-star—the charming, rumpled, self-effacing Chris O’Dowd—were particularly adept at this, whether walking the streets of East Williamsburg, scrolling through their respective ex’s Instagrams, or going on a roller-skating date at the LeFrak Center at Prospect Park. But in the end, movies are made of scripts, and occasionally Strouse would reel them back in. “I’d be like, ‘Okay, let’s do the movie you wrote?’”
When I asked Strouse to try to define her allure, he used words like “fierce honesty,” “wit,” and “charisma.” But what he eventually got to was Williams’ uncanny ability to be real. Or, more simply, to be herself. Of course not everyone’s real self is so appealing—but Williams’ real is dynamite.
“There is a moment [in The Incredible Jessica James] where she’s watching a kid’s performance and her eyes well up,” Strouse said of Williams. “It was just her and me and the camera and the VP—the kids were gone. And I thought, god, her mind is so powerful. She conjured up everything she needed to—I mean, my eyes were watering just watching her. She was […] bringing herself to that emotional place without having any person to work with.”
On 2 Dope Queens, Williams and her best friend/comedy partner, Phoebe Robinson, discuss “black lady love” and a host of quotidian and raunchy topics in front of live, sold-out crowds; on The Daily Show she was pure “J Willy,” as host Trevor Noah referred to her; and she brings a significant amount of her real self to Jessica James. I wondered if that meant she wouldn’t play a character radically different from herself—say, an army general from a different century.
“In some ways, it was okay to tell a kind of old-fashioned romantic-comedy story, because Jessica makes it all new.”
“Obviously, I would have to stop saying things like ‘totes preesh’ for a little while,” Williams quipped, which is an expression that Williams and Robinson use, and that Williams also says in Jessica James. But she’d figure it out. “How can I make that [character] feel relatable, and how can I be the most comfortable as that person?” Williams wondered of her hypothetical role. Suddenly I could imagine her as basically anything.
But The Incredible Jessica James did not demand that Williams make so dramatic a leap. And to the extent that it is safe and familiar—especially for someone accustomed to tackling any topic, no matter how challenging—I wondered if its simplicity had ever given her pause. “It took a lot of trust [in Jim] to do the movie, just because it’s such a sweet story,” Williams conceded. But that’s where Strouse’s implicit confidence in Williams counted. “In some ways,” he said, “it was okay to tell a kind of old-fashioned romantic-comedy story, because Jessica makes it all new.”
Through 2 Dope Queens, we know a not-insignificant amount about Williams’ personal life, due to the unbound places Robinson and Williams are readily willing to go. We know that Williams’ household was very Christian; that her first girl-boy party was in sixth grade, but instead of Blink-182 her parents provided gospel music (and a bouncy castle). Williams has told us she was in her “mid-twents” the first time she had sex; we know her boyfriend of three years is a photographer who is white.
But despite freely disclosing so much, Williams calls herself an introvert. She often prefers to stay home to play RollerCoaster Tycoon, and will move in and out of friend groups in order to remain independent, which, she says, “maybe isn’t the best quality.” Still, these are qualities she’s known most of her life. “Growing up, I would beat myself up for just wanting to curl up with a book, when really that was something that I didn’t need to beat myself up about in the first place. As I get older, I really try to honor the brilliant part of me that is introverted.”
As her stardom grows, and with the seeming necessity of using social media—which she does use regularly—I asked how she manages to maintain a truly private space.
“I’m still trying to figure that out,” she said. “And there are things that I do wanna keep private, because I am a pretty private person.” Which begs the question: how did a self-proclaimed introvert become a very public comedian who shares a lot about her personal life, despite an instinct to do otherwise?
“As I get older, I really try to honor the brilliant part of me that is introverted.”
“I think there’s two types of grandmas,” she began. “There’s the milk-and-cookies kind that you just love, and there’s the kind that swears and drinks beers and wants to go to Las Vegas.” Her own grandmother, Marsha, who passed away when Williams was 13, was the latter. When Williams stayed with her they would watch Saturday Night Live, Mad TV, South Park, and Space Ghost Coast to Coast. “She would watch everything, and I would stay up and watch a lot of that stuff with her. So I always saw comedy as a valid medium. If that kept her company, then that’s something that I really wanted to do.”
And opportunity came knocking for her to do so. The pivotal career moment came while Williams was finishing up her degree in creative writing and film at California State University, Long Beach. She was standing in line at Panda Express with a friend, ordering their favorite dish—orange chicken—when she picked up a call from her talent manager (she’d been sending out tapes and auditioning to get her start in the entertainment field).
Jon Stewart wanted to hire her full-time as part of The Best F#@king News Team Ever.
“We just started screaming in the cafeteria,” said Williams. “The only bad thing was that I had to finish my finals, and I didn’t care about my finals that semester at all.”
The Daily Show’s version of Williams’ hiring story is somewhat different than hers—she thinks they reached out to her after she sent an audition tape: they claim to have seen some other unknown video of her. “It’s always been up in the air. Seriously, like no one knows how I got hired, just that I did.”
And, ultimately, all that matters is that she did get hired. “My life completely changed for the better,” said Williams. “The show became sort of my family, and I learned a lot about myself when I was there, and the way I see the world, and what good work looks like.”
Williams’ final appearance on the show, with Trevor Noah now the host, came about a year ago on June 30, 2016. Jordan Klepper, standing with the rest of the correspondents said, “Jess, it has been an honor working with you. When I came in, I was so impressed by how young and talented you were, it almost made me angry.” Williams was not really trying to stop the tears from streaming down her face. “And now as you leave,” he continued, “I am honored to say that I am still pissed.”
Of that moment, Williams said she “felt a bunch of emotions that I needed to unpack with my therapist, Heather.” But any deeper sadness would be short lived; she already knew that she’d be shooting The Incredible Jessica James, and (spoiler/teaser alert) that she’d be developing a scripted comedy series. Plus, just a couple months prior, the first episode of 2 Dope Queens had aired on WNYC. It became the number one podcast on iTunes almost immediately.
“I like that she is nice. I wouldn’t say that I’m the mean one, but I’m certainly the judge-y one and she is more willing to give the benefit of the doubt. There’s a sweetness to her that I will never have, so I admire that.”
To that end, 2 Dope Queens might never happened had it not been for her stint on The Daily Show; Williams met her now co-host Phoebe Robinson while Robinson was doing background for a piece about black women’s hair in the military. “Basically that was fate because we talk about black hair [on the podcast] all of the time,” Robinson wrote in an email. The pair hit it off on set, because, according to Robinson, they both had backgrounds in improv and—though Robinson doesn’t any longer—white boyfriends. Robinson was running her own podcast out of her old apartment in Kensington and invited Williams to be a guest. By that time they’d become friends, and when Williams’ birthday approached, Robinson asked what she wanted to do. “She said she always wanted to try stand-up, so I asked her to co-host a monthly show I had at UCB East as a fun one-off.” Their stage chemistry was immediate, as it clearly still is.
Robinson says what she admires most about Williams is that she’s open to growing and to adventure. “She pushes herself, which is what we all have to do in order to survive and have fulfilling lives,” Robinson started, then added: “I like that she is nice. I wouldn’t say that I’m the mean one, but I’m certainly the judge-y one and she is more willing to give the benefit of the doubt. There’s a sweetness to her that I will never have, so I admire that.”
When I watched Jessica James alone, I was struck primarily by Williams’ remarkable realness, or whatever that glittering-yet-hard-to-define quality of hers is that landed her on TV at only 22 years old. On Williams’ last Daily Show appearance, Trevor Noah also struggled to describe her undeniably special essence. “This building is going to suffer a severe lack of”—he searched for the right word—“uh… J-Willy-ness without you.” To which Williams responded right away, through tears, “Mhm, mhm, I got a lot of Willy style.”
Watching the film with a live audience at BAM—I attended the screening Jim Strouse had been headed to on the train—I was struck not only by Williams, but by how funny the entire film is. As she and O’Dowd bantered, the audience regularly roared with laughter. If I had walked into that theater and seen my own face on the screen, seen the crowd loving it that much, I’d feel I could pretty much die knowing I’d done something right—knowing I’d made it. I imagined Williams in the audience at the same time, and wondered what she must be feeling as she watched a large audience watch her on a screen in giant form, in scene after scene.
“I’m getting all dressed up. I’m getting hair done, makeup done, and I always love that because that to me really feels like, ‘Oh, cool, I’m being an actor!’”
After the screening, Williams stood outside the theater doors, patiently and humbly taking on heaps of compliments from fans who were excited and nervous about meeting her. When I said hello, I told her we’d talked on the phone for this piece. Something like warm familiarity spread across her face and she said, “Oh yeah, we already know each other!” Her magnetism reads on screen, but it’s stunningly palpable in person.
It was a Tuesday afternoon when I originally spoke to Williams for this piece, and she was in a hotel room in Los Angeles, preparing to host an awards night for the organization Women In Film. Her mother was with her (“It’s a nice room, so I invited her to come stay”). At first, I’d been disappointed to be engaging from afar instead of meeting at a café in Clinton Hill where she lives, sipping on things and observing her in full form. But our conversation illuminated her ineffable grace, humor, and directness as much as any meeting could have. Even when talking about success, her unpretentious realness came through: “I’m getting all dressed up. I’m getting hair done, makeup done, and I always love that because that to me really feels like, ‘Oh, cool, I’m being an actor!’” It was a believable way to encapsulate “making it” for someone who had also just told me she was equally excited to be in L.A. for the warm meals that would be waiting for her at her family home.
At BAM, when an audience member too asked her about success, wondering if Williams had a particular moment when she felt she’d made it, she responded that she’d had one that very night: walking into her adopted hometown’s iconic theater, seeing a crowd of Brooklynites rapturously taking in a film she’s starring in. (I later saw a video on Williams’ Instagram that she’d captured in the still-dark theater as the end credits rolled, where she yells out, “Yaaaas! Brooklyn!”) But most of the time? Williams said everything just feels like normal life. She’s still just walking around being herself—she just happens to be incredible.
This feature appears in the Summer 2017 issue of Brooklyn Magazine, which hit the streets on June 17, 2017.
Photography by Jessica Yatrofsky. Styling by Alexis Badivi.
Hair: Ursula Stephens. Makeup: Rebecca Restrepo. Nails: Kylie Kwok.
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