Jessica Williams earned her stripes as one of The Daily Show's funniest and most effective correspondents with segments as incisive as they were confident. A nimble interviewer, Williams was more willing to use her opponent's strength against them than deliver the killing blow herself. But all along, her presence onscreen showed something like star power. And in The Incredible Jessica James, she fulfills that promise.
Jim Strouse wrote and directed The Incredible Jessica James, a Sundance darling picked up by Netflix and dropping today. He wrote the film with Williams in mind, and it shows: This is a millennial rom-com about a magnetic but struggling playwright who supports herself teaching and is trying to get over an ex. What makes Jessica unusual as a rom-com hero is clear from the title: She has none of the self-deprecating awkward "oops-my-purse" clumsiness that tends to plague the type. Jessica knows she's incredible. She's not surprised you think so too. She also considers herself witheringly honest — which creates some internal strain, since she wallpapers her apartment in rejection letters from people who don't agree with her self-assessment. If she clearly sees this as a phase that will lead to her eventual success, she does secretly fear that she might never make it.
If the character's greatness is asserted, it's never oversold. Jessica is a delight — an extended sequence of her silly-dancing testifies to her weirdness and strength — but she really isn't a great playwright yet (if the dialogue of her fantasy encounters with her ex are any indication). That's not quite the point, though. She's young and believes in theater passionately — so passionately that she emotionally blackmails one of the talented kids she works with for wanting to go to Six Flags instead of a writing retreat. Williams is a charismatic presence, but the flip side of being "incredible" is that you can also be judgmental and obnoxious, and she knows it. That she's 6 feet tall matters to her. She's thought about how to occupy her size. (And she uses her powers for good, even getting a manspreader on the subway to close his legs and make room.)
So where, you might ask, is the romance? That's the interesting thing about this film, which I've repeatedly referred to as a romantic comedy and should qualify as one. Jessica meets Boone — a newly divorced app creator played with hangdog charm by Chris O'Dowd — through her friend Tasha (Noël Wells). But their chemistry is minimal, and you won't end up caring much about the resolution. The movie skips the structure of the rom-com epiphany. There is no moment when love snaps into clarity, no airport chase, and the closest the film gets to an "I like you just the way you are" moment is when O'Dowd remarks — having read all her plays — that she's a very complicated person. It's not praise. It's not even approval. But she seems delighted. The film resists those old familiar buttons — the ones that resolve a film into True Love — and settles instead for an ambient well-meaning haze.
If this is a rom-com, then, the genre has strayed a long way from its origins. When you think of a typical rom-com heroine, you might imagine Meg Ryan's adorably ruffled feathers as she awaits her mystery man in You've Got Mail, or Sandra Bullock's sad little Christmas tree in While You Were Sleeping, or Renee Zellweger lip-synching Celine Dion's "All By Myself" in Bridget Jones' Diary. These are key moments that tap into something relatable and primordial about loneliness — these quiet glimpses into a woman's effort to construct a socially acceptable self, laced as they are with the potential for shame and failure.
But the rom-com heroine's solitude has changed along with the dating scene. It's not a coincidence that even in the Bridget Jones sequel, our protagonist hears the Celine Dion song she belted out in her twenties and switches without a thought to "Jump Around." The genre's single girls have gotten less diffident and lachrymose about their singlehood and their loneliness, and no one is less diffident than Jessica Williams' Jessica James.
While this obviously has something to do with millennials, online dating, and the ways we've learned to accommodate assertiveness, I think it owes something major to Judd Apatow's man-coms. One of Apatow's signature achievements in the early aughts was shredding the romance of the romantic comedy — one of the few vehicles that traditionally centered love (and women). In his hands, the formula became something closer to a coming-of-age story with love as a painful rite of passage. Typically, the dude lives in a state of arrested development; he loves weed and hanging out with his pals. (So does the camera: these are always the funniest, most rewarding scenes.) At some point the film joylessly recognizes that the hero needs to give all this up for adult love.
The "love" part of Apatow's rom-coms always felt a little hollow and, oh, medicinal. It took Jason Segal co-writing Forgetting Sarah Marshall with Apatow for a film to emerge that truly reconciled these two competing strands: the depressive freedom of being irresponsible and petty and "creative" with the vaguely redemptive invitation to improve that a certain kind of love story creates. Jessica James has a lot in common with Sarah Marshall: Both protagonists are would-be artists flailing as they try to get over an ex, and both love interests are messed up in their own way. These are movies about healing into versions of each other that can accept something like love — but the artistic dream will always come first.
That's a huge change. Remember: The crux of the rom-com had always been that the protagonist was (in one way or another) obsessed with love. They theorized it, lived it, slept it. Marisa Tomei's character in Only You starts the film by lecturing her students on soulmates, Meg Ryan can't stop thinking about Tom Hanks' sad love story in Sleepless in Seattle, and My Best Friend's Wedding is all about a woman who turns petty jealousy into a theory of love that awards it to the person with the prior claim.
Apatow's protagonists simply weren't obsessed in this way. That dramatically transformed the genre. A film tradition that had always been about capital-L Love had most of the love stripped out of it. It's been interesting to watch female-centric rom-coms follow in this tradition: Bridesmaids, for instance, is less about romantic love than it is about love between friends. As for The Incredible Jessica James, the extent to which Jessica never thinks about Boone is startling. Instead, her emotional energy is lavished on her ex (played by Atlanta's Lakeith Stanfield).
Williams carries this off beautifully. She plays Jessica as creative but resolutely unromantic — as a dreamer who cares about theater, and teaching theater, ostensibly because she believes in (and practices) creative experiments with honesty. That she routinely fails at the radical honesty she preaches makes her that much more believable (her greatest and most interesting failure might be the revelation that she broke up with the ex she pines for now — not because she was honest, but because she hoped he'd fight to keep her). The film nicely maps these little discrepancies between the character as she is and the artist she hopes to be, and Williams unfurls those imperfections in moments that feel as vulnerable as they are winsome.
It isn't a particularly compelling love story — the guy and the girl seem less passionate than (respectively) puzzled and bemused — but it is a fascinating portrayal of a black artist determined to make it. At a moment when most of our entertainment features anxiety and self-doubt, the most incredible thing about The Incredible Jessica James might be how easily its protagonist — rather than shrink, or blush, or self-deprecate — would shrug and likably agree.