Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like Dear Pillow

If you loved Dear Pillow, 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 Dear Pillow.

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#1
Uncle Kent

Uncle Kent

2011★ 5.3

Why watch this? A perfect follow-up to Dear Pillow for fans of Drama. It captures a similar light-hearted atmosphere.

A pothead kid's show cartoonist in Los Angeles spends a weekend trying to sleep with his visiting house guest - a woman from New York who he met on Chatroulette....

#2
The Merchant of Venice

The Merchant of Venice

2004★ 6.8

Why watch this? A perfect follow-up to Dear Pillow for fans of Drama. It captures a similar emotionally gripping atmosphere.

Venice, 1596. Bassanio begs his friend Antonio, a prosperous merchant, to lend him a large sum of money so that he can woo Portia, a very wealthy heiress; but Antonio has invested ...

#3
Boys Don't Cry

Boys Don't Cry

1999★ 7.4

Why watch this? A perfect follow-up to Dear Pillow for fans of Drama. It captures a similar emotionally gripping atmosphere.

A young transgender man explores his gender identity and searches for love in rural Nebraska....

#4
Waking Ned

Waking Ned

1998★ 7.1

Why watch this? A perfect follow-up to Dear Pillow for fans of Comedy. It captures a similar light-hearted atmosphere.

When a lottery winner dies of shock, his fellow townsfolk attempt to claim the money....

#5
The Men Who Stare at Goats

The Men Who Stare at Goats

2009★ 6.0

Why watch this? A perfect follow-up to Dear Pillow for fans of Comedy. It captures a similar light-hearted atmosphere.

A reporter in Iraq might just have the story of a lifetime when he meets Lyn Cassady, a guy who claims to be a former member of the U.S. Army's New Earth Army, a unit that employs ...

#6
Shutter Island

Shutter Island

2010★ 8.2

Why watch this? A perfect follow-up to Dear Pillow for fans of Drama. It captures a similar emotionally gripping atmosphere.

World War II soldier-turned-U.S. Marshal Teddy Daniels investigates the disappearance of a patient from a hospital for the criminally insane, but his efforts are compromised by tro...