Movies Like Gypsy and Charm

If you liked Gypsy and Charm (1989), a comedy movie directed by Takis Vougiouklakis, 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
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
2
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
3
One Night at McCool's (2001)
★ 5.9/10Also comedy
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
4
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
5
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
6
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
7
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
8
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…
9
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…
10
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
11
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
12
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
13
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
14
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
15
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.
16
Psych 2: Lassie Come Home (2020)
★ 7/10Also comedy
After Santa Barbara Police Chief Carlton Lassiter is ambushed and left for dead, Shawn and Gus return to help him and find themselves embroiled in a case involving the personal, the professional – and even the…
17
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
18
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
19
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.
20
Clear History (2013)
★ 6.1/10Also comedy
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.