Movies Like So You Want to Be a Gambler

If you liked So You Want to Be a Gambler (1948), a comedy movie directed by Richard L. Bare, 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
Easy Money (1983)
★ 6/10Also comedy
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
2
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends escape to a luxury spa retreat to reconnect, unwind and rediscover themselves, but their weekend of relaxation soon turns into a series of wild adventures and bad decisions.
3
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
4
The Audition (2015)
★ 6.2/10Also comedy
Robert De Niro and Leonardo DiCaprio must compete for the lead role in Martin Scorsese's next film.
5
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
6
Criminal (2004)
★ 6.2/10Also comedy
Needing a new partner capable of intricate cons, Richard Gaddis, recruits Rodrigo, a crook with a perfect poker face. The two plan a big-time scam: selling a fake Silver Certificate to currency collector William…
7
Ca$h (2010)
★ 5.9/10Also 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
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
9
A Bad Moms Christmas (2017)
★ 6.3/10Also comedy
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
10
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
11
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
12
Room Service (1938)
★ 6.5/10Also comedy
Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
13
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
14
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
15
The Three Stooges (2012)
★ 5.8/10Also comedy
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
16
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
17
Solid Serenade (1946)
★ 7.4/10Also comedy
Tom ties up Spike and sneaks into the courtyard of the glamorous Toodles Galore with his bass, hoping to woo her with his song, much to the annoyance of a sleeping Jerry.
18
Hard Luck (1921)
★ 6.9/10Also comedy
A down on his luck young man makes several attempts at committing suicide but fails them too. He then finds himself becoming more confident through a series of petty adventures, to such an extent that this becomes his…
19
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
20
Oliver the Eighth (1934)
★ 7.1/10Also comedy
Barbershop owners Stan and Ollie answer an ad in the newspaper from a wealthy widow looking for a husband. Ollie only mails in his response and is invited to the widow's mansion. Stan discovers his unmailed letter and…