Movies Like Chasing Fifty

If you liked Chasing Fifty (2015), a romance and comedy movie directed by Vojtěch Kotek, 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
Starting Over (1979)
★ 6.4/10Also comedy and romance
After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.
2
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
3
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
4
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
5
Butterflies Are Free (1972)
★ 6.8/10Also comedy and romance
Striving to be independent, the blind but determined Don Baker moves away from his overprotective mother. After settling into his new San Francisco digs, Don meets kooky neighbor Jill Tanner. Don's quick wit and good…
6
The Killer's Game (2024)
★ 6.4/10Also comedy
When top hitman Joe Flood is diagnosed with a terminal illness, he decides to take matters into his own hands – by taking a hit out on himself. But when the very hitmen he hired also target his ex-girlfriend, he must…
7
Cotton Comes to Harlem (1970)
★ 6.2/10Also comedy
Harlem's African-American population is being ripped off by the Rev. Deke O'Malley, who dishonestly claims that small donations will secure parcels of land in Africa. When New York City police officers Gravedigger…
8
Robin Williams: An Evening at the Met (1986)
★ 8.2/10Also comedy
In this hilarious stand up comedy, Robin Williams is energetic, witty and again hilarious. It's the number one stand up comedy of all time.
9
The Overnight (2015)
★ 5.9/10Also comedy
Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.
10
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…
11
Pretty Persuasion (2005)
★ 5.8/10Also comedy
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
12
Stretch (2014)
★ 6.2/10Also comedy
A hard-luck limo driver struggling to go straight and pay off a debt to his bookie takes on a job with a crazed passenger whose sought-after ledger implicates some seriously dangerous criminals.
13
Who Is Cletis Tout? (2001)
★ 5.9/10Also comedy
With a hitman’s gun aimed at him, Finch tells the story of how he broke out of jail, fell in love, and took the identity of a man wanted by the Mafia.
14
Accident Man: Hitman's Holiday (2022)
★ 6.8/10Also comedy
The Accident Man is back, and this time he must best the top assassins in the world to protect the ungrateful son of a mafia boss, save the life of his only friend and rekindle his relationship with his maniacal father…
15
Accident Man (2018)
★ 6.3/10Also comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
16
Showdown in Little Tokyo (1991)
★ 6.4/10Also comedy
An American with a Japanese upbringing, Chris Kenner is a police officer assigned to the Little Tokyo section of Los Angeles. Kenner is partnered with Johnny Murata, a Japanese-American who isn't in touch with his…
17
Over Your Dead Body (2026)
★ 6.4/10Also comedy
A dysfunctional couple head to a remote cabin to "reconnect", but each has secret intentions to kill the other.
18
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
19
South Park (Not Suitable for Children) (2023)
★ 7.4/10Also comedy
After it's discovered that a teacher at South Park Elementary has an OnlyFans page, Randy is compelled to take a closer look at the seedy underbelly of the world of online influencers.
20
Desperate Living (1977)
★ 6.3/10Also comedy
After killing her husband, Peggy Gravel and her murderous maid Grizelda wind up in the crazy town of Mortville, where Queen Carlotta presides over a sleazy collection of misfits.