Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like Chesterfield

If you loved Chesterfield, 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 Chesterfield.

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#1
Almost Friends

Almost Friends

2017★ 6.3

Why watch this? A perfect follow-up to Chesterfield for fans of Comedy. 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...

#2
How to Murder Your Wife

How to Murder Your Wife

1965★ 6.3

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

Stanley Ford leads an idyllic bachelor life. He is a nationally syndicated cartoonist whose Bash Brannigan series provides him with a luxury townhouse and a full-time valet, Charle...

#3
Cosi

Cosi

1996★ 6.1

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

Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overru...

#4
Big Stone Gap

Big Stone Gap

2014★ 5.9

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

A story centered around a transitional point in the life of Ave Maria Mulligan, the heart of her community in the Appalachian Mountains of Virginia....

#5
Thunderstruck

Thunderstruck

2012★ 6.1

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

After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an imp...

#6
A Nice Girl Like You

A Nice Girl Like You

2020★ 5.8

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

Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her...

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