Movies Like To Win the Lottery

If you liked To Win the Lottery (1970), a comedy movie directed by Dinos Dimopoulos, 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
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.
2
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…
3
Waking Ned (1998)
★ 7/10Also comedy
When a lottery winner dies of shock, his fellow townsfolk attempt to claim the money.
4
UHF (1989)
★ 6.7/10Also comedy
The eccentric new manager of a UHF television channel tries to save the station from financial ruin with an odd array of programming.
5
Bananas (1971)
★ 6.7/10Also comedy
When a bumbling New Yorker is dumped by his activist girlfriend, he travels to a tiny Latin American nation and becomes involved in its latest rebellion.
6
The Million Pound Note (1954)
★ 7/10Also comedy
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he…
7
Blank Check (1994)
★ 6/10Also comedy
Bullied by his siblings and nagged by his parents, 11-year-old Preston Waters is fed up with his family — especially their frugality. But he gets his chance to teach them a lesson when a money-laundering criminal…
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
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…
10
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
11
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…
12
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.
13
Footlight Parade (1933)
★ 6.8/10Also comedy
A fledgling producer finds himself at odds with his workers, financiers and his greedy ex-wife when he tries to produce live musicals for movie-going audiences.
14
The Twelve Chairs (1970)
★ 6.2/10Also comedy
In 1920s Soviet Russia, a fallen aristocrat, a priest and a con artist search for a treasure of jewels hidden inside one of twelve dining chairs, lost during the revolution.
15
Living in Oblivion (1995)
★ 7.2/10Also comedy
Low-budget independent filmmaker Nick Reve tries to keep everything together as his production is plagued with an insecure actress, a megalomaniac star, a pretentious beret-wearing director of photography, and lousy…
16
Eenie Meanie (2025)
★ 6.3/10Also comedy
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
17
Blackbeard's Ghost (1968)
★ 6.7/10Also comedy
The eponymous wraith returns to Earth to aid his descendant, elderly Emily Stowecroft. The villains want to kick Emily and her friends out of their group home so that they can build a crooked casino. Good guy Steve…
18
Monty Python's The Meaning of Life (1983)
★ 7.3/10Also comedy
Life's questions are 'answered' in a series of outrageous vignettes, beginning with a staid London insurance company which transforms before our eyes into a pirate ship. Then there's the National Health doctors who try…
19
Swindle (2014)
★ 7/10Also comedy
A boy named Griffin finds a valuable multi-million dollar baseball card. After accidentally selling the card for a million dollar loss, he enlists the help of his best friend Ben and his colleagues to regain the…
20
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.