Dynamic Watchlist Hub: Apr 10, 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
Under the Tuscan Sun

Under the Tuscan Sun

2003★ 6.9

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

Frances Mayes, a 35-year-old professor and writer from San Francisco, decides to take a tour of Tuscany following a difficult divorce. After impulsively buying a run-down villa in ...

#2
The Spectacular Now

The Spectacular Now

2013★ 6.7

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

Sutter, a popular party animal, unexpectedly meets the introverted Aimee after waking up on a stranger's lawn. As Sutter deals with the problems in his life and Aimee plans for her...

#3
Just Like Heaven

Just Like Heaven

2005★ 7.0

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

Shortly after David Abbott moves into his new San Francisco digs, he has an unwelcome visitor on his hands: winsome Elizabeth Masterson, who asserts that the apartment is hers -- a...

#4
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....

#5
Sacramento

Sacramento

2025★ 6.2

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

When free-spirited Rickey suddenly reappears in father-to-be Glenn’s life, the two former best friends embark on a spontaneous road trip from LA to Sacramento....

#6
Waiting to Exhale

Waiting to Exhale

1995★ 6.2

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

Cheated on, mistreated and stepped on, the women are holding their breath, waiting for the elusive "good man" to break a string of less-than-stellar lovers. Friends and confidants ...

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