Movies Like Clothes Make the Pirate

If you liked Clothes Make the Pirate (1926), a comedy movie directed by Maurice Tourneur, 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 Geisha Boy (1958)
★ 6.5/10Also comedy
Gilbert Wooley is a second-rate magician who is sent to entertain the troops in the pacific. During his time in Japan he becomes attached to a little orphan boy.
2
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.
3
Dog Gone (2008)
★ 6.5/10Also comedy
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
4
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedy
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…
5
Dennis the Menace (1993)
★ 5.9/10Also comedy
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
6
The Errand Boy (1961)
★ 6.2/10Also comedy
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty…
7
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
8
The Crimson Pirate (1952)
★ 7/10Also comedy
Burt Lancaster plays a pirate with a taste for intrigue and acrobatics who involves himself in the goings on of a revolution in the Caribbean in the late 1700s. A light hearted adventure involving prison breaks, an…
9
The Air Up There (1994)
★ 6.1/10Also comedy
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…
10
What Did You Do in the War, Daddy? (1966)
★ 5.9/10Also comedy
A by-the-book Captain is ordered to capture a strategic village in Italy. The Italian soldiers are willing to surrender, if they can have a festival first. The lieutenant convinces the Captain this is the only way…
11
The SpongeBob Movie: Search for SquarePants (2025)
★ 6.8/10Also comedy
Desperate to be a big guy, SpongeBob sets out to prove his bravery to Mr. Krabs by following The Flying Dutchman – a mysterious swashbuckling ghost pirate – on a seafaring adventure that takes him to the deepest depths…
12
Firehouse Dog (2007)
★ 6.2/10Also comedy
Rexxx, Hollywood's top canine star, gets lost and is adopted into a shabby firehouse. He teams up with a young kid to get the station back on its feet.
13
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
14
Take the Money and Run (1969)
★ 7.1/10Also comedy
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
15
Ace Ventura: When Nature Calls (1995)
★ 6.3/10Also comedy
Summoned from an ashram in Tibet, Ace finds himself on a perilous journey into the jungles of Africa to find Shikaka, the missing sacred animal of the friendly Wachati tribe. He must accomplish this before the wedding…
16
The Luck of the Irish (2001)
★ 6.1/10Also comedy
A teenager must battle for a gold charm to keep his family from being controlled by an evil leprechaun.
17
LaRoy, Texas (2024)
★ 6.8/10Also comedy
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.
18
The Wizards Return: Alex vs. Alex (2013)
★ 7.8/10Also comedy
While trying to prove to her family she can be mature and responsible, teen wizard Alex Russo conjures up a spell to rid herself of her bad qualities, unintentionally creating a Good and Evil Alex. When Evil Alex gets…
19
Rookie of the Year (1993)
★ 6.2/10Also comedy
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.
20
Little Big League (1994)
★ 6/10Also comedy
When 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…