Dynamic Watchlist Hub: Apr 16, 2026

10 Best Movies Like Play Boy

If you loved Play Boy, 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 Play Boy.

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#1
Love Don't Co$t a Thing

Love Don't Co$t a Thing

2003★ 7.6

Why watch this? A perfect follow-up to Play Boy for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool....

#2
Sidewalks of New York

Sidewalks of New York

2001★ 6.0

Why watch this? A perfect follow-up to Play Boy for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with sc...

#3
Love & Sex

Love & Sex

2000★ 6.1

Why watch this? A perfect follow-up to Play Boy for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of th...

#4
Cosi

Cosi

1996★ 6.1

Why watch this? A perfect follow-up to Play Boy for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overru...

#5
Jim & Andy: The Great Beyond

Jim & Andy: The Great Beyond

2017★ 7.5

Why watch this? A perfect follow-up to Play Boy for fans of Documentary & Comedy. It captures a similar light-hearted atmosphere.

Offbeat documentarian Chris Smith provides a behind-the-scenes look at how Jim Carrey adopted the persona of idiosyncratic comedian Andy Kaufman on the set of Man on the Moon....

#6
Mumford

Mumford

1999★ 6.5

Why watch this? A perfect follow-up to Play Boy for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quir...

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