Movies Like Sail a Crooked Ship
If you liked Sail a Crooked Ship (1961), a comedy movie directed by Irving Brecher, here are 19 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.
- 1
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.
- 2
Thunderstruck (2012)
★ 6.2/10Also comedyAfter 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.
- 3
Oscar (1991)
★ 6.4/10Also comedyAngelo "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…
- 4
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.
- 5
Married to the Mob (1988)
★ 6/10Also comedyAngela 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…
- 6
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedyPuppy 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…
- 7
Swindle (2014)
★ 7/10Also comedyA 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…
- 8
Welcome to Collinwood (2002)
★ 6.1/10Also comedyFive hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
- 9
American Dreamer (2022)
★ 6/10Also comedyIn 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.
- 10
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.
- 11
Rookie of the Year (1993)
★ 6.2/10Also comedyWhen 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.
- 12
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedyHawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
- 13
The Three Stooges (2012)
★ 5.8/10Also comedyLeft on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
- 14
The F**k-It List (2020)
★ 6/10Also comedyAfter 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.
- 15
Knight and Day (2010)
★ 6.2/10Also comedyA fugitive couple goes on a glamorous and sometimes deadly adventure where nothing and no one – even themselves – are what they seem. Amid shifting alliances and unexpected betrayals, they race across the globe, with…
- 16
Little Big League (1994)
★ 6/10Also comedyWhen the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
- 17
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.
- 18
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.
- 19
Taking Care of Business (1990)
★ 6.3/10Also comedyAn 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.