Dynamic Watchlist Hub: Apr 14, 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
Wake Up, Ron Burgundy: The Lost Movie

Wake Up, Ron Burgundy: The Lost Movie

2004★ 6.0

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

While Ron Burgundy's rivalry with Veronica Corningstone escalates quickly, a group of unprofessional thieves better known as 'The Alarm Clock' try to make the truth known, whatever...

#2
The Pirate

The Pirate

1948★ 6.4

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

A girl is engaged to the local richman, but meanwhile she has dreams about the legendary pirate Macoco. A traveling singer falls in love with her and to impress her he poses as the...

#3
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...

#4
Watching the Detectives

Watching the Detectives

2007★ 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.

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life fem...

#5
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....

#6
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...

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