Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Clothes Make the Pirate

If you loved Clothes Make the Pirate, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Clothes Make the Pirate.

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#1
The Geisha Boy

The Geisha Boy

1958★ 6.3

Why watch this? A perfect follow-up to Clothes Make the Pirate for fans of Comedy. It captures a similar light-hearted atmosphere.

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
The Errand Boy

The Errand Boy

1961★ 6.1

Why watch this? A perfect follow-up to Clothes Make the Pirate for fans of Comedy. It captures a similar light-hearted atmosphere.

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 acc...

#3
Taking Care of Business

Taking Care of Business

1990★ 6.3

Why watch this? A perfect follow-up to Clothes Make the Pirate for fans of Comedy. It captures a similar light-hearted atmosphere.

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....

#4
The Air Up There

The Air Up There

1994★ 6.2

Why watch this? A perfect follow-up to Clothes Make the Pirate for fans of Comedy. It captures a similar light-hearted atmosphere.

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 basketb...

#5
Beverly Hills Chihuahua 2

Beverly Hills Chihuahua 2

2011★ 5.9

Why watch this? A perfect follow-up to Clothes Make the Pirate for fans of Comedy. It captures a similar light-hearted atmosphere.

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 the...

#6
Jim Jefferies: Freedumb

Jim Jefferies: Freedumb

2016★ 7.3

Why watch this? A perfect follow-up to Clothes Make the Pirate for fans of Comedy. It captures a similar light-hearted atmosphere.

Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee....

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