
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.

Landline
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....

Almost Friends
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...

Lady Windermere's Fan
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....

Strictly Sexual
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....

Sidewalks of New York
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...

The Lords of Flatbush
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...