Movies like Sail a Crooked Ship (1961)
The best movies like Sail a Crooked Ship (1961) are Fun with Dick and Jane (1977), Thunderstruck (2012) and Oscar (1991). If Sail a Crooked Ship hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSwindle (2014)7.0/10 from 249 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Fun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisOscar (1991)
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 about to keep his promise.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDog Gone (2008)
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAmerican Dreamer (2022)
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.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisBeverly Hills Chihuahua 2 (2011)
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the tiny pups will stop at nothing to save them - because in good times and hard times, the family always sticks together. So Papi, Chloe and the puppies embark on a heroic adventure, proving once again that big heroes come in small packages.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMarried to the Mob (1988)
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe F**k-It List (2020)
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAnuvahood (2011)
Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSwindle (2014)
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 baseball card.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisWelcome to Collinwood (2002)
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisWrong Cops (2013)
A group of bad cops look to dispose of a body that one of them accidentally shot.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohnny Dangerously (1984)
An honest, goodhearted man is forced to turn to a life of crime to finance his neurotic mother's skyrocketing medical bills.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Air Up There (1994)
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home movie. But Saleh is the chief's son and has responsibilities at home, since the tribe's land is threatened by a mining company with its own hotshot basketball team.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Paper Tigers (2020)
Three middle aged men polish their martial arts skills to avenge their fallen master.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Ridiculous (2026)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRookie of the Year (1993)
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Trouble with Angels (1966)
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like Sail a Crooked Ship?
The closest matches to Sail a Crooked Ship are Fun with Dick and Jane (1977), Thunderstruck (2012) and Oscar (1991). Below are 17 more, each with the reason it matches.
What should I watch after Sail a Crooked Ship?
Start with Fun with Dick and Jane (1977), the closest match to Sail a Crooked Ship.
What is the highest-rated movie like Sail a Crooked Ship?
Swindle (2014), rated 7.0/10 by 249 TMDB users.
What is the newest movie like Sail a Crooked Ship?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Sail a Crooked Ship?
Yes: Fun with Dick and Jane (1977), Thunderstruck (2012) and Oscar (1991).
How are movies similar to Sail a Crooked Ship chosen?
First come films that Trakt’s viewers watch alongside Sail a Crooked Ship, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.