Movies Like Win, Place or Steal

If you liked Win, Place or Steal (1975), a comedy movie directed by Richard Bailey, 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
Dirty Mary Crazy Larry (1974)
★ 6.4/10Also comedy
Down-on-their-luck racers Larry and Deke steal from a supermarket manager to buy a car that will help them advance their racing chances. Their escape does not go as planned when Larry's one-night stand, Mary, tags…
2
Shadow of the Thin Man (1941)
★ 7/10Also comedy
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…
3
Tough Guys (1986)
★ 6/10Also comedy
Harry Doyle and Archie Lang are two old-time train robbers, who held up a train in 1956 and have been incarcerated for thirty years. After serving their time, they are released from jail and have to adjust to a new…
4
Last Vegas (2013)
★ 6.4/10Also comedy
Aging pals Billy, Paddy, Archie, and Sam have been best friends since childhood. When Billy finally proposes to his much-younger girlfriend, all four friends go to Las Vegas to celebrate the end of Billy's longtime…
5
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
6
Oscar (1991)
★ 6.4/10Also comedy
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…
7
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.
8
Uptown Saturday Night (1974)
★ 6.2/10Also comedy
Two blue-collar buddies search the underworld for a winning lottery ticket lost in a nightclub holdup.
9
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
10
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.
11
Fun with Dick and Jane (2005)
★ 6.2/10Also comedy
After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty…
12
Family Plot (1976)
★ 6.8/10Also comedy
Spiritualist Blanche Tyler and her cab-driving boyfriend encounter a pair of serial kidnappers while trailing a missing heir in California.
13
Horrible Bosses 2 (2014)
★ 6.2/10Also comedy
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
14
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
15
Big Trouble (2002)
★ 6.1/10Also comedy
The story of how a mysterious suitcase brings together, and changes, the lives of a divorced dad, an unhappy housewife, two hitmen, a pair of street thugs, two love struck teens, two FBI men and a psychedelic toad…
16
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…
17
Mystery Train (1989)
★ 7.3/10Also comedy
In Memphis, Tennessee, over the course of a single night, the Arcade Hotel, run by an eccentric night clerk and a clueless bellboy, is visited by a young Japanese couple traveling in search of the roots of rock; an…
18
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.
19
Planes, Trains and Automobiles (1987)
★ 7.3/10Also comedy
An irritable marketing executive, Neal Page, is heading home to Chicago for Thanksgiving when a number of delays force him to travel with a well meaning but overbearing shower curtain ring salesman, Del Griffith.
20
Lost in America (1985)
★ 6.9/10Also comedy
David and Linda Howard are successful yuppies from LA. When he gets a job disappointment, David convinces Linda that they should quit their jobs, liquidate their assets, and emulate the movie Easy Rider, spending the…