Movies Like Play It Safe

If you liked Play It Safe (2025), a crime and comedy movie directed by Jupiter Chapman, 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
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.
2
Wrong Cops (2013)
★ 6.1/10Also crime and comedy
A group of bad cops look to dispose of a body that one of them accidentally shot.
3
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…
4
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.
5
The Pickup (2025)
★ 6.4/10Also comedy and crime
A routine cash pickup takes a wild turn when mismatched armored truck drivers Russell and Travis are ambushed by ruthless criminals led by savvy mastermind Zoe.
6
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…
7
Thunderbolt and Lightfoot (1974)
★ 6.8/10Also comedy and crime
With the help of an irreverent young sidekick, a bank robber gets his old gang back together to organise a daring new heist.
8
Welcome to Collinwood (2002)
★ 6.1/10Also comedy and crime
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
9
Misdirection (2026)
★ 6.3/10Also 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…
10
Henry's Crime (2010)
★ 5.8/10Also crime and comedy
An aimless man is sent to prison for a crime he did not commit, an ex-con targets the same bank he was sent away for robbing.
11
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…
12
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.
13
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…
14
2 Guns (2013)
★ 6.5/10Also comedy and crime
A DEA agent and an undercover Naval Intelligence officer who have been tasked with investigating one another find they have been set up by the mob -- the very organization the two men believe they have been stealing…
15
Cotton Comes to Harlem (1970)
★ 6.2/10Also comedy and crime
Harlem's African-American population is being ripped off by the Rev. Deke O'Malley, who dishonestly claims that small donations will secure parcels of land in Africa. When New York City police officers Gravedigger…
16
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…
17
Absolution (2024)
★ 5.9/10Also crime
An aging ex-boxer gangster working as muscle for a Boston crime boss receives an upsetting diagnosis. Despite a faltering memory, he attempts to rectify the sins of his past and reconnect with his estranged children…
18
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.
19
Shadow of the Thin Man (1941)
★ 7/10Also comedy and crime
While attending a major horse race with their young son, Nick Jr., Nick and Nora Charles witnesse a shocking murder from the crowded grandstand. What first appears to be an isolated killing soon leads to a maze of…
20
Keanu (2016)
★ 6/10Also comedy and crime
Friends hatch a plot to retrieve a stolen cat by posing as drug dealers for a street gang.