Movies Like Chessky

If you liked Chessky (2021), a movie directed by Mischa Decurtins, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Taking Care of Business (1990)
★ 6.3/10
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
2
Much Ado About Nothing (2013)
★ 6.8/10
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
3
Sea Scouts (1939)
★ 6.4/10
Donald is an admiral on a seagoing voyage with his nephews in which they encounter a ravenous shark.
4
Bobby Jones: Stroke of Genius (2004)
★ 5.9/10
The story of golf icon and legend, Bobby Jones, who retired from competition at the tender age of 28.
5
Beau Hunks (1931)
★ 6.8/10
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
6
Winter Spring Summer or Fall (2024)
★ 7.3/10
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.
7
Fast Girls (2012)
★ 6/10
A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.
8
Hands of Stone (2016)
★ 6.6/10
The legendary Roberto Duran and his equally legendary trainer Ray Arcel change each other's lives.
9
Blue Chips (1994)
★ 6.1/10
Pete Bell, a college basketball coach is under a lot of pressure. His team isn't winning and he cannot attract new players. The stars of the future are secretly being paid by boosters. This practice is forbidden in the…
10
Jungleland (2020)
★ 6.4/10
Stanley manages his boxer brother Lion but when a devastating loss in the ring leaves the pair in debt, an opportunity to recoup the cash leads to a series of misadventures that threaten to break the bond between them.
11
Champagne Problems (2025)
★ 6/10
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
12
In the Blood (2014)
★ 5.8/10
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
13
The Best Man Holiday (2013)
★ 6.5/10
When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.
14
Paris, Wine & Romance (2019)
★ 6.9/10
Isabella is the ambitious new owner of her family’s Oregon winery whose dream of becoming world-renowned takes a big step forward when she enters a prestigious wine competition in Paris. Upon arrival, Isabella meets…
15
Our Wife (1931)
★ 7.1/10
Oliver is making plans to marry his sweetheart Dulcy with Stan as his best man, but the plans are thwarted when Dulcy's father sees a picture of Ollie and forbids the marriage. The couple plan to elope, and run away to…
16
Eleanor the Great (2025)
★ 6.8/10
94-year-old Eleanor Morgenstein tries to rebuild her life after the death of her best friend. As a result, she moves back to New York City after living in Florida for decades.
17
Towed in a Hole (1932)
★ 7/10
Although they are successful fishmongers, Stan convinces Ollie that they should become fishermen too, but making a boat seaworthy isn't an easy task.
18
My Dinner with Hervé (2018)
★ 6.3/10
An unlikely friendship evolves over one wild night in LA between a struggling journalist and actor Hervé Villechaize, the world's most famous gun-toting dwarf, resulting in life-changing consequences for both.
19
Coyote Ugly (2000)
★ 6.3/10
Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job…
20
29th Street (1991)
★ 6.9/10
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.