Movies Like Cups & Robbers

If you liked Cups & Robbers (2017), a comedy and crime movie directed by Jim Simone, 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
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.
3
Take the Money and Run (1969)
★ 7.1/10Also comedy and crime
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
4
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.
5
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…
6
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.
7
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.
8
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…
9
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.
10
68 Kill (2017)
★ 5.9/10Also comedy and crime
Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000.
11
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…
12
Two-Way Stretch (1960)
★ 6.7/10Also comedy and crime
Three criminals plan to break out of prison the day before their release in order to carry out a daring jewel robbery, intending to establish the perfect alibi by returning to jail afterwards. First however they must…
13
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…
14
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.
15
Bandits (2001)
★ 6.3/10Also comedy and crime
After escaping from prison, Joe and Terry go on a crime spree, robbing banks through Oregon and California in order to finance their scheme for a new life south of the border. Unfortunately, things get more complicated…
16
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.
17
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…
18
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…
19
The Protector (1985)
★ 5.9/10Also crime
Billy Wong is a New York City cop whose partner is gunned down during a robbery. Billy and his new partner, Danny Garoni, are working security at a fashion show when a wealthy man's daughter, Laura Shapiro, is…
20
Who Is Cletis Tout? (2001)
★ 5.9/10Also comedy and crime
With a hitman’s gun aimed at him, Finch tells the story of how he broke out of jail, fell in love, and took the identity of a man wanted by the Mafia.