I should start off by saying that Jessica Williams is a true star. She’s deeply charismatic, with a million-watt smile, soft-brown eyes, and armed with wit, attitude, and that old ’30’s standby, spunk. She imbues the sweet-natured The Incredible Jessica James with a fierce, vibrant heart.
The film follows a young, hip, and consistently-rejected young playwright through the travails of love and career. Kudos to writer/director Jim Strouse for spending an almost equal amount of time on his main character’s work as he does on her love life. James (Williams), stalled in her theatrical dreams and not quite over a breakup with her long-term boyfriend, goes on a date with a sheepish Irish app creator, Boone (the hangdog-faced Chris O’Dowd), who is so not over a recent divorce himself. The date becomes a one-night stand, but O’Dowd keeps hanging around, and Jessica finds she kind of likes him. As a way to help each other heal, they decide to unfriend their exes on social media and follow each other’s exes instead, which in a lesser movie, would lead to a variety of unfunny, farcical situations. Here it’s just a minor brushstroke, one of many in the whole picture.
Jessica runs a theater program for disadvantaged kids, a job she loves, even if it doesn’t pay well. So while she’s involved in theater for a living, it’s not the type of work she planned on doing, and how James navigates her own feelings of failure, while deeply enjoying the process of inspiring younger theater-makers, makes up the secondary plot. And thanks to a cameo by a certain playwright who will be familiar to theater-hounds, she gets a lesson on what a life in theater really means, which any thespian should aspire to.
Both plot strands, though kept separate, create the DNA of what the film is about: the search for identity and one’s place in the world and learning to be comfortable with what one finds. Jessica’s struggles could be that of any young twenty-something in any city. Boone, just as confused, is old enough to understand who he is and to accept that. James is not quite there yet.
The film often feels lackadaisical and meandering, yet here that’s more a compliment than a minus. Strouse loves his characters, and Williams in particular, so much so he lingers on their struggles and quirks, and we want to hang with them, too. The Incredible Jessica James, though set in fast-paced New York City, feels more like a slow, meandering day by the river where you can set down your picnic blanket, take out some wine and cheese, and just bask in the moment. And with Jessica Williams luring you to stay for a bit, that’s just what you want to do.