Movies Like Sweepstakes Winner

If you liked Sweepstakes Winner (1939), a comedy movie directed by William C. McGann, 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
Racing Stripes (2005)
★ 6/10Also comedy
Shattered illusions are hard to repair -- especially for a good-hearted zebra named Stripes who's spent his life on a Kentucky farm amidst the sorely mistaken notion that he's a debonair thoroughbred. Once he faces the…
2
Let It Ride (1989)
★ 6.3/10Also comedy
An average kind of guy who has a slight problem with gambling goes to the track, and mystically, it seems as though he can't lose, no matter how he bets; and he has an incredible day.
3
From Noon Till Three (1976)
★ 6/10Also comedy
Bank robber Graham Dorsey spends a few hours with beautiful widow Amanda Starbuck, in which time his gang takes part in a disastrous holdup. Learning of his comrades' demise, Dorsey goes on the lam. Believing her…
4
Dirty Rotten Scoundrels (1988)
★ 7.1/10Also comedy
Con artist Lawrence Jamieson is a longtime resident of a luxurious coastal resort, where he enjoys the lavish fruits of his deceptions -- that is, until a competitor, Freddy Benson, shows up. When the new guy's lowbrow…
5
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…
6
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.
7
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
8
The Hustle (2019)
★ 6.2/10Also comedy
Two female scam artists, one low rent and the other high class, compete to swindle a naïve tech prodigy out of his fortune. A remake of the 1988 comedy "Dirty Rotten Scoundrels."
9
Monte Carlo or Bust! (1969)
★ 5.9/10Also comedy
Sequel to "Those Magnificent Men In Their Flying Machines". This time an international car rally from England to Monte Carlo provides the comedic farce.
10
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…
11
Tom and Jerry: The Fast and the Furry (2005)
★ 7.1/10Also comedy
After being evicted from their old house by Tom's owner for causing major damage, cat and mouse Tom and Jerry enter a race entitled the "Fabulous Super Race" to win a mansion.
12
The Distinguished Gentleman (1992)
★ 6/10Also comedy
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
13
Rat Race (2001)
★ 6.3/10Also comedy
In an ensemble film about easy money, greed, manipulation and bad driving, a Las Vegas casino tycoon entertains his wealthiest high rollers -- a group that will bet on anything -- by pitting six ordinary people against…
14
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.
15
Take the Money and Run (1969)
★ 7.1/10Also comedy
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
16
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.
17
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…
18
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
19
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.
20
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…