The word “trouble” captures the essence of The Trouble with Jessica, a darkly comedic and wildly chaotic story that spirals into mayhem during one unforgettable dinner party. Divided into chapters, all with “The Trouble with…” in their titles, the initial chapter introduces the titular flirtatious (and irritating) dinner guest. As the night goes on, the titles—including one on moving a dead body through London at night—reflect the increasing turmoil. The ensemble is tossed into a pressure cooker of secrets, lies, backstabbing, heartfelt confessions, and sheer panic as writer/director Matt Winn serves up a bizarre and hilarious exploration of guilt, friendship, and the desperate lengths people will go to to protect themselves from their unjustifiable decisions.
The Trouble with Jessica kicks off with a dinner party hosted by Sarah (Shirley Henderson, Harry Potter and the Goblet of Fire) and Tom (Alan Tudyk, Resident Alien) at their soon-to-be-sold home. They’ve invited their best friends, Beth (Olivia Williams, Dune Prophecy) and Richard (Rufus Sewell, The Diplomat), but Beth spoils the mood right away by bringing Jessica without first clearing it with the hosts. Sarah detests Jessica (Indira Varma, Game of Thrones), a bestselling author and friend of the foursome from college, whose overly provocative behavior with Tom rubs Sarah raw.
The simmering tension explodes when Jessica dishes up disturbing descriptions of each of the friends, digging the knife in particularly deep when she targets Sarah. Jessica’s sharp tongue skewers Jessica’s fragile psyche, and Jessica calling her out is the cookie that makes Sarah crumble. Sarah’s been dealing with her own personal drama involving Tom’s financial shenanigans, and Jessica’s stirring of the pot turns the dinner party into a nasty version of Seinfeld’s Festivus.
Trouble boils over when Jessica makes a drastic choice that sets off a string of increasingly desperate reactions. The friends, now without Jessica’s input, spiral through a chaotic maelstrom of panicked design-making.
The initial “The Trouble with” chapters are just the appetizers for a main course that stirs in a nosy neighbor, the arrival of dessert-loving cops, and the completely unexpected visit from the potential buyers, Klaus and Ellen. Klaus’ work has kept him out of the country, and he’s leaving again, thus the surprise visit at the most inopportune time. Can men have “resting b*tch face?” The internet is divided on the answer, but Klaus definitely has one. Is he impressed with the house? There’s no way of knowing, apart from the occasional “okay” he tosses into the conversation.
It’s due to Klaus’ visit that The Trouble with Jessica slides into screwball comedy territory. And it works because Max Winn cast actors who can adeptly handle switching in and out of disparate genres without missing a beat.
Winn and co-writer James Handel blend absurd predicaments and a little slapstick in a truly poignant relationship drama. The circumstance, withheld to avoid a spoiler, that launches the foursome into a criminal cover-up is grim and results in long-held resentments bubbling to the surface. The claws come out and old wounds are reopened, but the script’s loaded with enough dark humor and witty dialogue to keep the story from getting too intense. Sharply written and briskly paced, The Trouble with Jessica is a hilarious dive into the limits of friendship, the flexible nature of morals, and the healing power of a particularly delicious dessert.
GRADE: B
Running Time: 89 minutes
Release Date: April 25, 2025 (Limited)
Distributor: Music Box Films
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