Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Sideways

If you loved Sideways, 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 Sideways.

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#1
Playing It Cool

Playing It Cool

2014★ 5.9

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

A young man meets and instantly falls in love with an engaged woman....

#2
Looking: The Movie

Looking: The Movie

2016★ 7.2

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

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships ...

#3
Murphy's Romance

Murphy's Romance

1985★ 6.1

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

Emma, a divorced single mother seeking to start her life over, moves to a small town in Arizona. She befriends Murphy, the older local pharmacist, but things turn complicated when ...

#4
Factotum

Factotum

2005★ 6.2

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

This drama centers on Hank Chinaski, the fictional alter-ego of "Factotum" author Charles Bukowski, who wanders around Los Angeles, CA trying to live off jobs which don't interfere...

#5
The Sisters Brothers

The Sisters Brothers

2018★ 6.8

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

Oregon, 1851. Hermann Kermit Warm, a chemist and aspiring gold prospector, keeps a profitable secret that the Commodore wants to know, so he sends the Sisters brothers, two notorio...

#6
Tom Jones

Tom Jones

1963★ 5.9

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

Tom loves Sophie and Sophie loves Tom. But Tom and Sophie are of differering classes. Can they find a way through the mayhem to be true to love?...

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