Movies Like Winnie's Vacation
If you liked Winnie's Vacation (1927), a comedy movie directed by Ralph Ceder, 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
Babes (2024)
★ 6/10Also comedyAfter 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.
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Eenie Meanie (2025)
★ 6.3/10Also comedyA 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.
- 4
29th Street (1991)
★ 6.9/10Also comedyAfter 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.
- 5
Eddie Izzard: Dress to Kill (1999)
★ 7.8/10Also comedyEddie Izzard takes her show to San Francisco to give a brief history of pagan and Christian religions, the building of Stonehenge, the birth of the Church of England and of Western empires, and the need for a European…
- 6
Driver's Ed (2026)
★ 6.9/10Also comedyA group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
- 7
Godspell (1973)
★ 6.7/10Also comedyIn modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
- 8
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
- 9
Dog Gone (2008)
★ 6.5/10Also comedyA courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
- 10
Sextuplets (2019)
★ 6.2/10Also comedyFather-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.
- 11
Fun with Dick and Jane (1977)
★ 6.6/10Also comedyWhen an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
- 12
National Lampoon's Vacation (1983)
★ 7.1/10Also comedyClark Griswold is on a quest to take his family to the Walley World theme park for a vacation, but things don't go exactly as planned.
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YES DAY (2021)
★ 6.7/10Also comedyA mom and dad who usually say no decide to say yes to their kids' wildest requests — with a few ground rules — on a whirlwind day of fun and adventure.
- 14
Mickey and Minnie Wish Upon a Christmas (2021)
★ 7/10Also comedyAfter a series of mishaps, Mickey, Minnie and the gang are separated all over the world and must try to get back to Hot Dog Hills by Christmas Eve. A mysterious and jolly stranger shows up to tell them about The…
- 15
Mouse Cleaning (1948)
★ 6.9/10Also comedyMammy Two-Shoes threatens to throw Tom out of the house if he makes a mess. Jerry sees an opportunity to rid himself of his feline nemesis.
- 16
Hollywood or Bust (1956)
★ 6.2/10Also comedyThe last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the…
- 17
Duplex (2003)
★ 6.1/10Also comedyWhen a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
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The Willoughbys (2020)
★ 7.1/10Also comedyWhen the four Willoughby children are abandoned by their selfish parents, they must learn how to adapt their Old-Fashioned values to the contemporary world in order to create something new: The Modern Family.
- 19
The Wonderful World of Mickey Mouse: Steamboat Silly (2023)
★ 6.9/10Also comedyMickey and gang must stop hundreds of old film reel versions of Mickey from wreaking havoc all over town.
- 20
Spa Weekend (2026)
★ 6.5/10Also comedyFour lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…