Movies Like The Trouble with Jessica

If you liked The Trouble with Jessica (2024), a comedy and drama movie directed by Matt Winn, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Breaking News in Yuba County (2021)
★ 5.9/10Also comedy and drama
An overlooked pencil-pusher catches her husband in bed with another woman, the shock of which causes him to die of a heart attack. So she buries his body and takes advantage of the growing celebrity status that comes…
2
Cheap Thrills (2013)
★ 6.4/10Also comedy and crime
Recently fired and facing eviction, a new dad has his life turned upside down when he meets a wealthy couple who offer a path to financial security... but at a price.
3
Savage House (2026)
★ 7/10Also comedy and drama
Against the backdrop of 18th century England, a massive pox outbreak, and Jacobite uprising – Sir Chauncey Savage and Lady Savage blindly pursue a better life. It's not without a tinge of irony that their family name…
4
Withnail & I (1987)
★ 7.2/10Also comedy and drama
Two out-of-work actors -- the anxious, luckless Marwood and his acerbic, alcoholic friend, Withnail -- spend their days drifting between their squalid flat, the unemployment office and the pub. When they take a holiday…
5
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy and crime
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
6
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also crime and comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
7
Small Apartments (2012)
★ 5.9/10Also comedy and crime
When a clumsy deadbeat accidentally kills his landlord, he must do everything in his power to hide the body, only to find that the distractions of lust, the death of his beloved brother, and a crew of misfit characters…
8
Friendship (2025)
★ 6.4/10Also comedy and drama
Suburban dad Craig falls hard for his charismatic new neighbor Austin, and his attempts to make an adult male friend threatens to ruin both of their lives.
9
Guns Up (2025)
★ 6.5/10Also comedy and crime
When a job goes horribly wrong, an ex-cop and family man who moonlights as a mob henchman has one night to get his family out of the city.
10
The Joneses (2010)
★ 6.2/10Also comedy and drama
A seemingly perfect family moves into a suburban neighborhood, but when it comes to the truth as to why they're living there, they don't exactly come clean with their neighbors.
11
Funny People (2009)
★ 5.9/10Also comedy and drama
Famous and wealthy funnyman George Simmons doesn't give much thought to how he treats people until a doctor delivers stunning health news, forcing George to reevaluate his priorities with a little help from aspiring…
12
Dinner at Eight (1933)
★ 6.8/10Also comedy and drama
An ambitious New York socialite plans an extravagant dinner party as her businessman husband, Oliver, contends with financial woes, causing a lot of tension between the couple. Meanwhile, their high-society friends and…
13
Four Lions (2010)
★ 7/10Also comedy and crime
Four Lions tells the story of a group of British jihadists who push their abstract dreams of glory to the breaking point. As the wheels fly off, and their competing ideologies clash, what emerges is an emotionally…
14
Panic (2000)
★ 6.2/10Also crime and drama
Alex is going through a midlife crisis and it has become a very difficult time for him. His marriage is struggling, he's worried about his son, and his job of killing people for his family has become the most stressful…
15
After the Thin Man (1936)
★ 7.4/10Also comedy and crime
After returning to San Francisco, Nick and Nora Charles are drawn into the disappearance of Nora’s cousin’s husband. When he is found murdered, suspicion falls on the troubled family, and Nick reluctantly resumes his…
16
Seance on a Wet Afternoon (1964)
★ 7.3/10Also crime and drama
Working-class British housewife Myra Savage reinvents herself as a medium, holding seances in the sitting room of her home with the hidden assistance of her under-employed, asthmatic husband, Billy. In an attempt to…
17
Blindspotting (2018)
★ 7.3/10Also comedy and crime
Collin must make it through his final three days of probation for a chance at a new beginning. He and his troublemaking childhood best friend, Miles, work as movers, and when Collin witnesses a police shooting, the two…
18
Jawbreaker (1999)
★ 6.4/10Also comedy and crime
When an exclusive clique of teenage socialites accidentally murder their best friend on the morning of her birthday, the three girls responsible conspire to hide the truth.
19
Saltburn (2023)
★ 6.9/10Also drama and comedy
Struggling to find his place at Oxford University, student Oliver Quick finds himself drawn into the world of the charming and aristocratic Felix Catton, who invites him to Saltburn, his eccentric family's sprawling…
20
Wildflower (2023)
★ 7.4/10Also comedy and drama
The story of Bea Johnson from birth to graduation as she navigates life with an intellectually disabled parent and an extended family who can't quite agree on the best way to help.