Movies Like The Big Win

If you liked The Big Win (1911), a comedy movie, 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
The Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
2
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
3
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
4
Olaf's Frozen Adventure (2017)
★ 6.5/10Also comedy
Olaf is on a mission to harness the best holiday traditions for Anna, Elsa, and Kristoff.
5
The Railrodder (1965)
★ 6.8/10Also comedy
After literally swimming across the Atlantic Ocean, an Englishman takes a country trip across Canada on a railcar.
6
The Tramp (1915)
★ 6.5/10Also comedy
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
7
Once Upon a Snowman (2020)
★ 6.9/10Also comedy
The previously untold origins of Olaf, the innocent and insightful, summer-loving snowman are revealed as we follow Olaf’s first steps as he comes to life and searches for his identity in the snowy mountains outside…
8
The Bank (1915)
★ 6.3/10Also comedy
A janitor at a bank is in love with a secretary and dreams that she has fallen in love with him too.
9
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
10
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.
11
Mickey's Steam Roller (1934)
★ 6.4/10Also comedy
While streetworker Mickey romances Minnie, Mickey's nephews Morty and Ferdie take control of his steamroller and it's full speed ahead on a very destructive ride.
12
Perfect Day (1929)
★ 7/10Also comedy
Two families embark on a pleasant Sunday picnic but manage to run into a variety of issues with their temperamental automobile. Each incident requires repeated exits and reboardings by Laurel, Hardy, their wives and…
13
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.
14
Up and Away (2018)
★ 6.1/10Also comedy
Hodja is a dreamer. He wants to experience the world, but his father insists he stays home and takes over the family's tailor shop. Fortunately, Hodja meets the old rug merchant El Faza, who gives him a flying carpet…
15
Our Wife (1931)
★ 7.1/10Also comedy
Oliver is making plans to marry his sweetheart Dulcy with Stan as his best man, but the plans are thwarted when Dulcy's father sees a picture of Ollie and forbids the marriage. The couple plan to elope, and run away to…
16
Thicker Than Water (1935)
★ 7.4/10Also comedy
Oliver's in trouble with his wife after missing a payment on their furniture, having given the money to Stanley, who used it instead to pay Mrs. Hardy for his room and board. At Stan's suggestion Ollie then withdraws…
17
Chips Ahoy (1956)
★ 6.7/10Also comedy
Chip and Dale are starving in their tree home when they notice a plentiful supply of acorns on an island in a lake. To get to the island, they borrow a miniature model ship of Donald's to sail on. The irate Donald…
18
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
19
Barbie (2023)
★ 6.9/10Also comedy
Barbie and Ken are having the time of their lives in the colorful and seemingly perfect world of Barbie Land. However, when they get a chance to go to the real world, they soon discover the joys and perils of living…
20
Towed in a Hole (1932)
★ 7/10Also comedy
Although they are successful fishmongers, Stan convinces Ollie that they should become fishermen too, but making a boat seaworthy isn't an easy task.