The Incredible Jessica James Is a Breakout Turn for Jessica Williams

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Chris O’Dowd and Jessica Williams in The Incredible Jessica James. Photo: Netflix

The Incredible Jessica James is a little odd duck of a film, an old-fashioned romantic comedy that’s decidedly modern in its frame of reference, a character-driven piece that never lets us too deep into its protagonist, a movie as pleasant as it is fleeting. It is a quintessential Netflix film — in other words, a movie you can’t imagine getting a platform anywhere else, for (mostly) better or worse.

But above all else, it’s a strong argument for Jessica Williams, former Daily Show breakout, as a cinematic avatar for a certain kind of city-dwelling, creative 20-something. That much is clear from its rollicking title sequence, in which Jessica dances around her charmingly ramshackle Bushwick apartment in the style of bygone ’90s sitcoms, probably pretending she’s in the opening number of the very kind of movie she’s in. It’s such a lovely, life-affirming portrait of young adulthood that has nothing to do with consuming or binge drinking or ’gramming avocado toast. The Incredible Jessica James will not be a cynical movie, and we know this for certain all of five minutes in.

Jessica is an aspiring yet mostly failed playwright, who makes ends meet working at a nonprofit children’s theater workshop. She’s also getting over a bad breakup with Damon (Lakeith Stanfield), her puppy-dog-eyed ex who keeps showing up uninvited in her daydreams. To kick her blues, her sassy white best friend Tasha (Noël Wells) hooks her up with Boone (Chris O’Dowd,) a sad-sack divorcé who is as unsure about getting back into the dating game as she is. Even though they don’t immediately click on a romantic level, they bond as friends and as a two-person support group for their respective emotional flounderings.

As much as Jessica James is about post-breakup heartache, the film itself never wallows, and neither does Jessica much, at least outwardly. Director-writer James C. Strouse instead focuses on Jessica as a figure of resilience, who only begins to have doubts about what it’s all for in the film’s final act. This is mostly quite refreshing; the last thing the world needs is another portrait of a navel-gazing quarter-lifer. Nor do we need to see Jessica’s dramatic aspirations comically inform the plot or the style of the film, which they don’t: Jessica simply really loves the theater, the way another person might really love music or carpentry or accounting. A conversation late in the film with playwright Sarah Jones (playing herself) is uniquely moving in its lack of neuroses: “You love it, and you’re doing it,” Jones tells her. “That’s kind of it.”

Perhaps Jessica James errs too much on the side of breeziness, then: We never dig too deep into the circumstances of her and Damon’s breakup, nor what kind of plays she writes, nor even her eventual attraction to Boone. I can’t say that I was individually pining for any of these familiar themes to be expounded upon, but collectively, one leaves the film wondering what, exactly, it wanted to get across. The film’s most prickly and elliptical sequence is a visit to Ohio for Jessica’s sister’s baby shower, which begins with a delightful Jackie Brown airport walkway homage and quickly deflates into an awkward family reunion in which which Jessica’s misfit status is painted in spare but effective strokes. Her stubborn bravado takes on new pathos from there — in the middle of an argument with Boone, he admits he “really likes her,” and she responds, with not a small amount of exhaustion, “Of course you do! Everyone does. I’m freaking dope.”

What makes Jessica truly dope, though, by the end of the film, is not her ability to get over her ex or to charm her new lover, or even her skills as a playwright, but her commitment to the kids she teaches. So many lesser films would use her scenes with her class as an outlet for frustration, but Strouse uses it as a device for hope — even if every grant and fellowship rejects her, she has a chance with her kids. Somehow, of all the romances in this romantic comedy, that one is the most palpable onscreen, and a subplot involving her most promising student is the most emotionally convincing. Your mileage may vary on whether or not you leave the film wishing Jessica was your girlfriend or best friend, but you will almost certainly wish she was your drama teacher.

The Incredible Jessica James Is Jessica Williams’s Breakout