Dynamic Watchlist Hub: Apr 12, 2026

10 Best Movies Like Winston

If you loved Winston, 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 Winston.

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#1
Landline

Landline

2017★ 6.1

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

A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair....

#2
Almost Friends

Almost Friends

2017★ 6.3

Why watch this? A perfect follow-up to Winston for fans of Comedy & Drama. 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...

#3
Lady Windermere's Fan

Lady Windermere's Fan

1925★ 6.8

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

A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved....

#4
Strictly Sexual

Strictly Sexual

2008★ 6.1

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

Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes....

#5
Sidewalks of New York

Sidewalks of New York

2001★ 6.0

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

The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with sc...

#6
The Lords of Flatbush

The Lords of Flatbush

1974★ 5.8

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

Set in 1958, the coming of age story follows four lower middle-class Brooklyn teenagers known as The Lords of Flatbush. The Lords chase girls, steal cars, shoot pool, get into stre...

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