Movies Like Gentlemannagangstern

If you liked Gentlemannagangstern (1941), a comedy and crime movie directed by Weyler Hildebrand, 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
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…
2
The Jönsson Gang & Dynamite Harry (1982)
★ 6/10Also comedy and crime
Sickan, Vanheden and Rocky try to rob the Berns nightclub one night, but Vanheden has made the mistake to invite his constantly drunk cousin, the old dynamiter Dynamite-Harry and he ruins the plan. Sickan is arrested…
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
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…
5
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.
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
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…
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
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 $68,000.
10
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also crime and comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
11
Married to the Mob (1988)
★ 6/10Also comedy and crime
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and…
12
How to Rob a Bank (2007)
★ 5.8/10Also comedy and crime
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
13
Icefall (2025)
★ 6.6/10Also crime
A young Indigenous game warden arrests an infamous poacher only to discover that the poacher knows the location of a plane carrying millions of dollars that has crashed in a frozen lake. When a group of criminals and…
14
Accident Man (2018)
★ 6.3/10Also crime and comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
15
Ca$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…
16
Trouble (2024)
★ 6.7/10Also comedy and crime
Wrongfully convicted of murder, a clumsy electronics salesman faces police corruption and criminal conspiracies in an attempt to prove his innocence.
17
Red Right Hand (2024)
★ 6.6/10Also crime
Cash is trying to live a quiet, honest life in a small Appalachian town. When a vicious crime boss forces him back into her services, he soon learns he's capable of anything -- even killing -- to protect his family and…
18
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.
19
Hostile Takeover (2025)
★ 6.9/10Also comedy
Follows Pete, a professional hitman, as he faces a group of assassins after the boss of a crime syndicate suspects disloyalty due to his attendance at Workaholics Anonymous meetings.
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.