Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like Pretty Sad

If you loved Pretty Sad, 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 Pretty Sad.

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#1
The Girl in the Book

The Girl in the Book

2015★ 5.8

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

The story of a young writer's transformation when her past invades her present....

#2
Imperial Dreams

Imperial Dreams

2014★ 6.6

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

A 21-year-old reformed gangster's devotion to his family and his future is put to the test when he is released from prison and returns to his old stomping grounds in Watts, Los Ang...

#3
The Trials of Cate McCall

The Trials of Cate McCall

2013★ 6.4

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

In order to be reinstated to the bar and recover custody of her daughter, a hotshot lawyer, now in recovery and on probation, must take on the appeal of a woman wrongfully convicte...

#4
Sky

Sky

2015★ 6.2

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

A woman embarks on a journey alone across the United States after fleeing from her violent husband....

#5
Tigertail

Tigertail

2020★ 6.7

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

A man reflects on the lost love of his youth and his long-ago journey from Taiwan to America as he begins to reconnect with his estranged daughter....

#6
Luckiest Girl Alive

Luckiest Girl Alive

2022★ 6.5

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

A successful woman in New York City finds her life upended when she is forced to confront a dark truth that threatens to unravel her meticulously crafted life....

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