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“The Trouble with Jessica” Needs More Trouble

Written by: Christopher Llewellyn Reed | April 25th, 2025

The Trouble with Jessica (Matt Winn, 2023) 2½ out of 5 stars

Director Matt Winn’s The Trouble with Jessica features some amusing moments that bounce around the screen with occasionally frenetic energy. When not careening out of control, the plot settles into a paradoxical monotony. Is this drama? Is this comedy? Does it know? There is nothing wrong with hybrid storytelling, except that each element should at least be aware of the other.

The film features a powerhouse cast. Shirley Henderson (See How They Run), Rufus Sewell (Old), Alan Tudyk (Netflix’s Resident Alien series), Olivia Williams (The Father), and Indira Varma (Crisis) play the lead roles, with assorted supporting actors joining in as needed. Mostly a chamber piece stuck in one space for the bulk of the runtime, The Trouble with Jessica relies heavily on dialogue, which the cast chews on with gusto. They’re good, but can’t quite rise above the limits of the script.

l-r: Indira Varma, Olivia Williams, Alan Tudyk, Shirley Henderson, and Rufus Sewell in THE TROUBLE WITH JESSICA. Courtesy of Music Box Films.

We start with a dinner party, two couples and an extra fifth (the titular woman), all friends from college. Jessica (Varma) is a successful author, the exciting rebel of the group who never settled down. Sarah (Henderson) and Tom (Tudyk) host in their gorgeous, multistory London pad. The other two are Beth (Williams) and Richard (Sewell).

Sarah can’t stand Jessica, and wishes she would stop flirting with Tom all the time (who really doesn’t seem to mind). Beth is besties with Jessica, and Richard enjoys the ruckus she causes. Emotions run high in the first part of the meal.

l-r: Indira Varma, Rufus Sewell, and Alan Tudyk in THE TROUBLE WITH JESSICA. Courtesy of Music Box Films.

Until Jessica exits to the garden and hangs herself (nothing a look at the trailer doesn’t reveal). Turns out her externally carefree demeanor masked a depression. For a variety of reasons, the remaining four don’t call the police (though they’ll show up later, anyway, to somewhat comic relief). Part of the problem is that Sarah and Tom are financially under water thanks to the latter’s poor decisions and really need to sell the house quickly. A scandal, they fear, would ruin things.

There are more secrets afoot, promising delicious details in the ensuing mayhem. And there are, in fact, plenty of laughs. Unfortunately, there are also a lot of maudlin sequences not quite emotionally supported by earlier events.

l-r: Alan Tudyk and Shirley Henderson in THE TROUBLE WITH JESSICA. Courtesy of Music Box Films.

In the end, The Trouble with Jessica is a decidedly uneven soufflé (rather than a clafoutis, source of an admittedly funny recurring gag within the movie), rising in parts to engage and then collapsing in less successful sections. The manic activities of the ensemble notwithstanding, the collective effect proves rather inert. There’s just not quite as much trouble as promised.

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Christopher Llewellyn Reed is a film critic, filmmaker, and educator, as well as Film Festival Today's Editor. A member of both the Online Film Critics Society (OFCS) and the Washington DC Area Film Critics Association (WAFCA), and a Rotten Tomatoes-approved film critic, Chris is, in addition, lead film critic at Hammer to Nail and the author of Film Editing: Theory and Practice.

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