Movies Like The Personal Life of Mr. Phelps

If you liked The Personal Life of Mr. Phelps (1987), a comedy and crime movie directed by David E. Tolchinsky, 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
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.
2
One Night at McCool's (2001)
★ 5.9/10Also comedy and crime
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
3
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.
4
Simpsley (2026)
★ 8.1/10Also comedy and crime
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment…
5
Trap House (2025)
★ 6.6/10Also crime
An undercover DEA agent and his partner embark on a game of cat and mouse with an audacious, and surprising group of thieves – their own rebellious teenagers, who have begun robbing from a dangerous cartel, using their…
6
Breathless (2012)
★ 5.9/10Also comedy and crime
Lorna is a strong-willed Texas woman who’s had enough of her untrustworthy husband Dale’s criminal acts and lack of husbandry. Fed up, she enlists the help of her old friend, Tiny, to help her figure out what to do…
7
Ca$h (2010)
★ 5.9/10Also crime and comedy
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a…
8
Misdirection (2026)
★ 6.2/10Also crime
A desperate couple have pulled off a string of high-end break-ins to pay off a mob debt. When they attempt to rob their latest victim, they find themselves caught in a deadly game of cat and mouse. The tables are…
9
Accident Man (2018)
★ 6.3/10Also crime and comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
10
Song of the Thin Man (1947)
★ 6.7/10Also comedy and crime
While attending a glamorous jazz cruise on New York’s East River, Nick and Nora Charles witness the fatal shooting of a wealthy patron. When suspicion falls on a young bandleader and his musicians, the couple steps in…
11
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy and crime
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
12
The Dream Team (1989)
★ 6.1/10Also comedy and crime
Four mental patients on a field trip in New York City must save their caring chaperone, who ends up being taken to a hospital in a coma after accidentally witnessing a murder, before the killers can find him and finish…
13
How to Rob a Bank (2007)
★ 5.8/10Also comedy and crime
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
14
Married to the Mob (1988)
★ 6/10Also comedy and crime
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and…
15
The Cheap Detective (1978)
★ 6.4/10Also comedy and crime
A spoof of the entire 1940s detective genre. San Francisco private detective, Lou Pekinpaugh is accused of murdering his partner at the instigation of his mistress—his partner's wife.
16
Bottle Rocket (1993)
★ 6.2/10Also comedy and crime
Dysfunctional friends Dignan and Anthony plan and execute a robbery with their pot-growing friend, Bob. The short film that inspired Wes Anderson’s feature debut.
17
Sheroes (2023)
★ 5.8/10Also comedy and crime
When four thick-as-thieves friends arrive in Thailand, they quickly find themselves in over their heads. Fighting to stay alive, they employ their unique set of skills and unleash their fierce loyalty in a…
18
In the Blood (2014)
★ 5.8/10Also crime
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
19
The System (2022)
★ 7.3/10Also crime
When a young soldier, newly returned from war, gets caught up in a drug bust, he is recruited by the authorities to go undercover in a notoriously dangerous prison in order to figure out what is really going on.
20
LaRoy, Texas (2024)
★ 6.8/10Also crime and comedy
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.