Sep 7 2017 12:00pm

The Incredible Jessica James Is Actually Incredible

The Incredible Jessica James

In a world where everything seems to suck, we need a good romantic comedy again. Netflix has been promoting The Incredible Jessica James as such. It’s a feature-length film that follows a fictional character played by Jessica Williams. Williams has gained notoriety for her role as a senior correspondent for the Daily Show. The Incredible Jessica James is a taste of her comedy in a larger form with a fair amount of mating, dating, and love—as well as a strong arc of finding oneself in the murky waters of Millennial adulthood.

The film opens with Jessica James (Williams) on a Tinder date going wrong, just as she’s trying to get over her ex-boyfriend Damon (Lakeith Stanfield). In her day-to-day life, Jessica runs a children’s theater workshop encouraging children in NYC to become playwrights. Jessica herself is a playwright, trying to break into the industry and create art that she cares about. It’s just gotten significantly harder since her breakup. After a fair amount of wallowing and witty introspective banter, Jessica’s best friend Tasha (Noël Wells) sets her up on a date.

Boone (Chris Dowd) is a man with an accent and a newly minted divorce. Their date is the picture-perfect example of two people trying to move on who are stuck in the past and, frankly, don’t want to be set up. But things take a surprising turn as Jessica and Boone deign to be honest with each other. This honesty sets them up for a solid post-date hookup, and a tentative, awkward friendship that includes cyber-stalking each other’s exes.

As Jessica continues to mull over her relationship with Damon and the playwriting fellowships pile up, she images Damon popping into her life, and the ways in which things went wrong. She sees the way her sister and family are happy in their traditional lives and relationships, too. Jessica can’t help but ponder what she needs to do for personal fulfillment. At the same time, Boone seems to become an increasing presence in her life, and she finds that someone who’s equally as fragile, broken, and smarmy as her may have something new to offer.

First thing’s first: this film is an amazing film that’s not a traditional romantic comedy. The ending is not about the romance and is a pretty strong HFN. The last scene of the film makes it clear that the romantic arc leads to a positive outcome, but it also puts the focal point of the film on Jessica’s growth as a person, her friendships, and her nonprofit work. It’s honestly refreshing because the film takes the time to make Jessica as fully-rounded of a character as possible. This movie is more Sleepless in Seattle than, say, Pretty Woman or 27 Dresses, and I think it worked wonderfully as a result.

It sparkles immediately because of the wit. The writing of the film (James C. Strouse) is acerbic and on-point with the way people in their 20’s speak today. It’s not a film that attempts to make itself feel “universal.” The lines on the surface can sound almost as parodies of themselves, yet they work toward a greater momentum in the film that’s decidedly serious without being too earnest.

Williams is also a brilliant actress and comedian. She takes the writing and really molds it to her will. She’s able to get across every breath of sarcasm, of secret joy and heartache. I think any viewer will come away praising her talents – she’s just that good, and this film is if nothing else a vehicle for those talents to be displayed. Her character is a gentle commentary on the overworked, struggling Millennial. She’s talented and intelligent, cynical, and all too aware of social justice and the struggles of the world…yet still highly individualistic when it comes to some major parts of her life. It’s a character that’s real and will resonate. The opening scene of the film, where Jessica sees her ex at the bar she picked for her bad Tinder date, is a great example of the writing and how Williams interprets it.

JESSICA: It’s great to see you’ve moved on already, after only…two and a half months of not dating.

DAMON: Three and a half months, actually. But…

HEATHER: Hi. I’m Heather.

JESSICA: I’m sure you are.

It’s a line that’s both so ridiculous and so brilliant. Williams delivers that “I’m sure you are” with a straight face, an almost imperceptible smile. It made me love the film right away—because how do you not like someone who’s clearly feeling so much and is able to distill it in such a biting way?

They’re both so awkward and ridiculous that it makes the romance feel natural even as the rest of the plot unfolds.

The Incredible Jessica James is a departure from other romantic comedies in this way, too. Jessica as a heroine is much more mellow than her frazzled white-woman counterparts ala Bridget Jones. There’s still a large character arc based on recognizing personal insecurities; but the film is much less focused on the idea of moving toward romance and more about moving toward acceptance and achievement. It’s a positive sign of the space we’re in now culturally, but it’s also something that clearly benefits from the presence of Williams.

The romance is understated, but the character of Boone, and Dowd’s portrayal of him, is pretty great. He’s delightfully pathetic, and I can’t say I’ve ever shipped a romance where I’d use that phrase to describe the hero. Boone’s foil to Jessica is in his awkward attempts at moving through life. Whereas Jessica has periodic daydreams about Damon but never actually confronts him about their breakup, Boone’s shown doing some very minor, bumbling snooping on his wife and her new boyfriend. He’s funny, self-deprecating, and sympathetic. What I like best is that he clearly plays along with Jessica and her unrepentant desire to be herself. Their banter is quality shit.

JESSICA: By the way, I am loving your ex-wife’s Instagram. Her photos are so good. Food photography really is an art. It’s just the dabblers I don’t care about.

BOONE: Yeah. Food porn is one of my top two favorite porns.

JESSICA: What’s your other favorite porn?

BOONE: Uh………Human.

They’re both so awkward and ridiculous that it makes the romance feel natural even as the rest of the plot unfolds. It’s also a pleasure that Boone, while cute and worthy of a romantic plotline, is not at the center of all of Jessica’s struggles. Her self-fulfillment doesn’t rely on him, and it makes her successes throughout the film so much more meaningful.


I think the overall structure of the film is satisfying, although it could easily have been an extra 10 minutes long and I would have been delighted. It’s tightly written and tightly plotted, so as a result I think we miss out on some secondary characters getting a bit more screen time, and likely a few more dialogue zingers. It’s also worth noting that Jessica and Boone are never officially “dating” in an exclusive, monogamous way throughout the film. There is some tension in that, but it’s also very realistic to how people date right now, particularly two people who are trying to overcome deep-seated emotions from recent breakups.

People who expect a romance arc that includes Boone and Jessica being physically/emotionally monogamous will likely not be happy with some elements of the romance plotline, but it’s honestly not a huge element of the film, it’s addressed when necessary, and it actually serves to further their romance because of how it relates to people trying to break up with significant others.

The Incredible Jessica James is the witty modern comedy the world needs right now. For anyone who wants comedy that’s far away from many of today’s sitcoms and “bromance” movies, this film is the ideal palate cleanser. It’s intelligent, thoughtful, mellow and, most of all, it feels organic in the way that it unfolds. I haven’t watched a film in a long time that’s felt so natural in the flow of its characters and plot. Jessica and Boone are also a couple that challenge some traditional romance conceptions, and their banter is top-notch. Anyone looking for a movie to watch that will have them chuckling and appreciating Williams’s comedy and character development should take the time to watch it. The Incredible Jessica James is rewarding and warm, and I really hope it’s a herald for other films of its kind. 

H&H Editor Picks:

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September 2017 Romance Novels New Releases Shopping List






John is a student, reviewer, and editor with a taste for social justice. He's queer/LGBTQ and has always loved a good romance novel. A current student at Ithaca College, he is majoring in Integrated Marketing Communications and trying to pick up a creative writing minor on the side. If you observe him in the wild, you may see him reading—or find him watching reruns of The Golden Girls while sipping his first/second/third cup of coffee for the day. You can find his reviews on his blog, Dreaming in Books, and listen to his random musings on Twitter @DreamingReviews.

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Heather Waters
1. HeatherWaters
You got me! Bumping up in my queue. This sounds like just the thing.
Jen Wattley
2. JenWattley
I absolutely agree, John! I watched this movie this weekend and I was utterly charmed. Everyone's so weird in an unapologetic way. I love how Jessica relates to the kids. I love how I relate to her from the perspective of someone who's now out of their 20s, and I LOVE the banter between Jessica and Boone. Now I feel like I need to go and read it again.
3. wsl0612
Chris Dowd, EEEE!! Ever since the IT Crowd I'm a great fan! He has such wonderful comic timing, but is still so earnestly sweet. Not the usual smirky, self-satisfied comedian (no, no, I don't mean you Mr. SNL alum, not at all).
5. willaful
Great write up! Hey, now we need the guy who plays Moss in a rom-com! I love him!

So... am I the only person who thought the ending of the movie was one of Jessica's dreams? But that it shows her growth because it's a happy dream, rather than one mired in the past.
Jen Wattley
6. JenWattley
@willaful--I thought it was a fantasy too, but I'm so glad it wasn't. It really illustrates Jessica's growth.

And yes, same about Richard Ayoade. I really like him.
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