Some roles feel like they were specifically written for someone – in that they embody the role so perfectly that you couldn’t imagine anyone else playing them – and The Incredible Jessica James’s eponymous lead character (played by Jessica Williams) is definitely one of them. The Daily Show standout shines in the film, playing a 20-something budding playwright with endearing charisma and infectious humour.
The film is a character piece more than anything, allowing Williams to showcase her comedic talent, but the story is one we’ve seen time and time again – a romantic dramedy about a struggling artist in New York. While she frequently receives rejection letters from the theatre companies she hopes to show her plays, she teaches playwriting to kids at a local nonprofit theatre. She’s also dealing with a recent breakup from her long-term boyfriend, Damon (Lakeith Stanfield), who she is evidently still in love with. We understand her tumultuous feelings towards Damon through a series of dream sequences – adding a welcome slice of surrealism to an otherwise conventional film.
To help get over him, her best friend Tasha (Noël Wells) sets her up on blind date with divorced app developer Boone (Chris O’Dowd, playing a charming romantic lead reminiscent of his role in Bridesmaids). With both of them still hung up over their exes, they find it easy to be completely honest with each other – and soon the relationship progresses from talking about their past loves to genuinely enjoying time with each other.
In the wrong hands, Jessica would be a lot more unlikeable – she’s brutally honest bordering on insensitive, she’s overly confident bordering on arrogant, she’s brash and unrelenting. We see this in the very first scene, where she openly criticizes her date’s attempts at flirting both in person and on Tinder, and then admits she’s only going out with him to make her ex jealous. She also knows she’s cool and it’s a welcome surprise to see a woman so confident in herself. In a climactic fight between the romantic leads, Boone says he really likes her – without skipping a beat, Jessica replies “Of course you do. Everybody does. I’m freaking dope.” Spoken by anyone else, I would find that line disgustingly cocky, but with Williams it’s just downright hilarious. Williams possesses an impeccable comedic timing that not only makes the character extremely likeable, but also incredibly captivating – without reservations, you just feel compelled to see where the story takes her.
Despite Williams’s effortlessly brilliant performance, I still feel like I don’t know Jessica James. Towards the end, Boone reads all of Jessica’s plays and tells her that she’s “a very complicated person”. If only we got to see what her plays were like – because it only seems like the film scratches the surface level of her issues and anxieties. We’re given a glimpse of something deeper when she goes home to her conservative family in Ohio, in a hilarious scene where she questions the patriarchy in a baby shower – but again, it’s only a glimpse and I don’t really understand if Jessica overcame any struggles by the end of the film outside of her love life.
Even though The Incredible Jessica James is conventional in its storytelling – drawing comparisons with other stories about struggling artists in New York (Frances Ha, Girls, Master of None), it’s nevertheless a boundlessly endearing indie with a star-making performance from Jessica Williams.