With a smile as sharp as sharp as her wit, and a delivery as cutting as her side-eye, comedian Jessica Williams quickly became a fan favorite on The Daily Show, to the point where rabid watchers were demanding she get the hosting gig when Jon Stewart announced he’d be stepping down. But Williams didn’t want that. She had plans of her own, and among them is Jim Strouse’s The Incredible Jessica James, a heartfelt comedy created for, starring, and executive produced by Williams.
Strouse and Williams first worked together on his charming 2015 dramedy People Places and Things, which starred Flight of the Conchords’ Jemaine Clement as a graphic novelist struggling to find love, raise his daughters, inspire a classroom of students, and pull his professional life together in the wake of a devastating break-up. Williams had a only small role in the film, but it was enough to convince Strouse he needed to make his next movie around her. And so he constructed the story of Jessica James, a playwright who is struggling to find love, inspire a classroom of students, and pull her professional life together in the wake of a devastating break-up. Okay. The Incredible Jessica James is essentially a genderwapped, race-bent remake of Strouse’s last movie, with Williams upgraded from eye-rolling supporting character to troubled hero. Still, it’s undeniably charming.
Williams stars as Jessica James, an aspiring playwright who loves theater “the way other people love sports or food,” which is to say passionately, to the point of self-destruction. She ties herself in knots teaching a group of grade schoolers how to channel their feelings into drama for the stage. She decorates her walls not only with playbills and show posters, but also with the rejection letters received from playhouses who’ve refused her submissions. And she’s quick to dismiss those she feels can’t match her passion for her work. All this has left the lonely New Yorker desperate enough to accept a blind date with a recent divorcee.
Lucky for Jessica, her oversexed lesbian gal pal (Noël Wells, brandishing vibrators with all the subtlety Strouse’s script offers, which is to say none) steers her right with Boone (Chris O’Dowd). Despite a disastrous first date made up mostly of awkward forthrightness, the unfortunately named love interest smiles, “I enjoyed being honest with you.” And then in a bit of TMI that fits the vibe, Boone confesses that he’s gifted at cunnilingus. So, they end up back at his place. But Jessica is quick to split after. A warm, rich, older and vaguely doughy white man is a decent rebound from her devastatingly handsome and emotionally available struggling artist ex Damon (Lakeith Stanfield), but she can’t seriously date him, right?
The pairing looks ridiculous, and both Jessica and Boone know it. They have little in common. And what’s worse, they’re both still hung up on their last loves, offering to Strangers on A Train their Instagram stalking, by following each other’s exes and reporting back if anything alarming comes up. (Mostly it’s masterful food pics and custom-made phone case shots.) But as odd a couple as they seem, Williams and O’Dowd’s chemistry is undeniable.
Yet Strouse battles against the urge to make this a rom-com, pulling Jessica away from Boone into some undercooked subplots. Running from romance as a road to happiness, Jessica throws herself into her work, pushing one young writer to the point of bullying. Addicted to the drama on the stage, Jessica has made her life a thing of extremes. She needs big moments, big wins, or else she feels failure, and so hangs another rejection letter on her wall.
We see Jessica chafe at conformity when she impulsively buys a jazzy purple flight suit to wear on a visit to her Ohio hometown. And to show her loathing of the weirdly acceptable party games of baby showers, screaming heavy metal music rages over scenes of primly dressed surbanites playing the dreaded dirty diaper/candy bar game. But this jaunt out of New York comes and goes at a sprint, unceremoniously dropping Jessica back into pushing to find career validation from kids instead of her writing. (Oddly, the only bit of her writing we get to see are juvenile fantasy sequences where Damon bursts into her life with cornball confessions and poorly plotted suicide attempts.) All this gambols into a conclusion that aims for subversive but comes off silly and over-earnest, as if a happy ending that firmly brings Jessica and Boone together would be caving to the conformity this hard-headed heroine loathes.
I get the impulse. The surface-level feminist thing to do is not hinge Jessica’s happiness or self-discovery on her getting a man. But with more nuance and thought, you can give the girl both. In Bridesmaids, the finale’s chief goal was healing the bond between longtime girl friends. Getting the guy was the cherry on top, not the main objective. But The Incredible Jessica James gets skittish, offering some dissatisfying half-stepping on the romance thread’s conclusion. Considering one of Jessica’s major issues was her fear of commitment and the complacency of a long-term relationship, this feels like a story decision made for message instead out of character. And the film suffers for it.
Overall, The Incredible Jessica James is pretty wonky, delivering a story that’s heart is big, but that’s path is meandering. Still, Williams makes it sing. Whether she’s dressing down a pushy Tindr date, firmly demanding her bestie to not masturbate while they talk on the phone, or dances madly about her apartment building to a song only she can hear, she is enthralling. O’Dowd is reliably affable, and even a bit sexy as the enthusiastic lover who avoids the tired “what do you do for a living” question with a more apt for NYC version, “How do you pay your rent?” And their star powers combined carry us through Strouse’s more sanctimonious and sentimental moments.
The Incredible Jessica James hits Netflix on July 28th.