Dynamic Watchlist Hub: Apr 19, 2026

10 Best Movies Like Gypsy and Charm

If you loved Gypsy and Charm, 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 Gypsy and Charm.

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#1
Lessons in Chocolate

Lessons in Chocolate

2007★ 5.9

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

Mattia, a building contractor on a promising career path, is about to close the biggest deal of his professional life, when his illegally-hired worker Kamal falls off some scaffold...

#2
Adventures in Public School

Adventures in Public School

2018★ 6.3

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

A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes....

#3
Jim Jefferies: Freedumb

Jim Jefferies: Freedumb

2016★ 7.3

Why watch this? A perfect follow-up to Gypsy and Charm 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....

#4
Little Italy

Little Italy

2018★ 6.6

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

Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?...

#5
Tom Segura: Disgraceful

Tom Segura: Disgraceful

2018★ 7.1

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

Tom Segura gives voice to the sordid thoughts you'd never say out loud, with blunt musings on porn, parking lot power struggles, parenthood and more....

#6
Almost Friends

Almost Friends

2017★ 6.3

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

A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a s...

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