Movies Like Chekhov in Yalta

If you liked Chekhov in Yalta (1988), a comedy and drama movie directed by Donald McWhinnie, 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
Lady Windermere's Fan (1925)
★ 6.9/10Also comedy and drama
A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.
2
Girl in the Box (2016)
★ 6.7/10Also drama and tv movie
The true story of 20-year-old Colleen Stan, a hitchhiking woman abducted by a young couple and held captive for seven years, during which time she's tortured and forced to live as a slave to her captors.
3
Hooking Up (2020)
★ 6.3/10Also comedy and drama
Bailey and Darla embark upon a misguided and mutually deceitful form of therapy, one in which they must drive across the country, re-enacting Darla's colorful history as a sex addict. As their true motivations for the…
4
A Flintstones Christmas Carol (1994)
★ 6.8/10Also comedy and tv movie
Fred is cast as Ebenezer Scrooge in a stage adaption of the classic Christmas story, but is acting a bit stingy in real life.
5
Barbarians at the Gate (1993)
★ 6.9/10Also comedy and drama
F. Ross Johnson decides to buyout his own tobacco firm RJR Nabisco after the plans of the launch of his new product, a smokeless cigarette Premier, fail on account of market rumours.
6
Cheaters (2000)
★ 6.3/10Also drama and tv movie
In the fall of 1994, a teacher at Chicago's run-down Steinmetz High conspires with the school's academic decathlon team to cheat on an academic competition.
7
Clear History (2013)
★ 6.1/10Also comedy and tv movie
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
8
My Own Love Song (2010)
★ 6.2/10Also comedy and drama
A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.
9
Rebound: The Legend of Earl 'The Goat' Manigault (1996)
★ 7.1/10Also drama and tv movie
A dramatization of the life of Earl 'The Goat' Manigault (Don Cheadle), with a lot of factual based occurrences. A reformed junkie returns from prison to clean up his act and devote the rest of his life to the young…
10
SubUrbia (1997)
★ 6.2/10Also comedy and drama
A group of suburban teenagers try to support each other through the difficult task of becoming adults.
11
Alley Cats Strike (2000)
★ 6/10Also drama and comedy
A group of hip retro teenage outsiders become involved in an interschool bowling rivalry.
12
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
13
Family Weekend (2013)
★ 6.3/10Also comedy and drama
A 16-year-old girl takes her parents hostage after they miss her big jump-roping competition.
14
Psych: The Movie (2017)
★ 7.2/10Also comedy and tv movie
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and…
15
Welcome Home Roscoe Jenkins (2008)
★ 6/10Also comedy and drama
When a celebrated TV show host returns to his hometown in the South, his family is there to remind him that going home is no vacation!
16
Landline (2017)
★ 6.2/10Also comedy and drama
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
17
The House of Tomorrow (2019)
★ 6.8/10Also drama and comedy
The film tells futurist, architect, and inventor R. Buckminster Fuller's incredible story through two teens hoping to get laid, become punk gods, and survive high school.
18
Good Luck Charlie, It's Christmas! (2011)
★ 6.7/10Also comedy and drama
Teddy Duncan's middle-class family embarks on a road trip from their home in Denver to visit Mrs. Duncans Parents, the Blankenhoopers, in Palm Springs. When they find themselves stranded between Denver and Utah, they…
19
Ray Donovan: The Movie (2022)
★ 6.8/10Also drama and tv movie
A showdown decades in the making brings the Donovan family legacy full circle. As the events that made Ray who he is today finally come to light, the Donovans find themselves drawn back to Boston to face the past. Each…
20
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.