Movies Like Damned If You Do, Damned If You Don't

If you liked Damned If You Do, Damned If You Don't (2025), a comedy movie directed by Gianni Di Gregorio, 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
Ma che bella sorpresa (2015)
★ 5.9/10Also comedy
High school professor Guido is a hopeless romantic whose life falls apart after his girlfriend leaves him. Paolo, a former student of his, helps him in getting out of his depression for a better chance to become a PE…
2
A Girl in Australia (1971)
★ 6.7/10Also comedy
The film is about an old fashioned Italian with moral values of the 1930/40's , who has to find a wife in the modern, woman's liberated society of Australia of the 1960/70's.
3
Don't Stop Me Now (2019)
★ 6.3/10Also comedy
Paola, a modern woman used to the hardships of modern life, takes her chance to make things right for herself.
4
He's Worse than Me (1985)
★ 6.3/10Also comedy
Two reckless friends Leonardo (Adriano Celentano) and Luciano (Renato Potstsetto) are just doing whatever they want and getting into endless alterations. When one of them decides to marry, their friendship is in a…
5
Thus Spoke Bellavista (1984)
★ 7.9/10Also comedy
In Naples, Professor Bellavista is a retired man, passionate about the philosophy and thought of Ancient Greece. Every day, in his luxurious apartment, he teaches his lessons of life to the poor-nothing (his friends)…
6
Kidz (2020)
★ 6/10Also comedy
Sara and Nicola are married and in love. Their lives seem to be perfect: they have an angelic six-year-old daughter, thriving careers and a stable marriage. The birth of their second child, which disrupts the family…
7
My Best Enemy (2006)
★ 6.1/10Also comedy
When a neurotic hotel manager fires a maid for allegedly stealing a laptop, her son swears revenge and begins to expose his deepest secrets — only to regret it after falling for his daughter.
8
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
9
Ignorance Is Bliss (2017)
★ 5.9/10Also comedy
Ernesto and Filippo, two high school teachers, couldn’t be more different: Filippo is a cheerful liberal who is constantly online. Handsome and youthful, he is a serial seducer on the social networks. Ernesto, instead…
10
The New Monsters (1977)
★ 7/10Also comedy
A collection of dark-humoured vignettes, including tales of a cardinal with a liberal congregation, a motorist and a hitchhiker, mentally challenged tramps, parents contemplating their daughter's participation in a…
11
Too Much (1986)
★ 6.5/10Also comedy
Oscar dreams of becoming an actor or a stuntman. To contact a manufacturer he stages an accident and consequently injures a young actress, then tries to limit the damage by taking the girl to his home.
12
A Beautiful Day (2026)
★ 5.9/10Also comedy
Tommaso, a single father of four, has shut himself off from the world. When his daughters push him to start over, he meets Lara — a brilliant, captivating woman. But both carry secrets that could change everything.
13
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!
14
Special Features: Handsome (1983)
★ 5.9/10Also comedy
Forty-something Mattia has every woman in town lusting after him. But every time a woman wants to get hitched, he drags out his 'daughter' (actually the girl next door) to pass judgment on this woman.
15
Dennis the Menace (1993)
★ 5.9/10Also comedy
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
16
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.
17
Thunderstruck (2012)
★ 6.2/10Also comedy
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 important lesson.
18
I Can Quit Whenever I Want (2014)
★ 7.4/10Also comedy
A university researcher is fired because of the cuts to university. To earn a living he decides to produce drugs recruiting his former colleagues, who despite their skills are living at the margins of society.
19
The Thursday Murder Club (2025)
★ 6.6/10Also comedy
A group of senior sleuths passionate about solving cold cases get plunged into a real-life murder mystery in this comic crime caper.
20
The Monster (1994)
★ 6.9/10Also comedy
A vicious serial sex killer is on the loose, and landscape gardener and shop-window outfitter Loris is the prime suspect, thanks to his unfortunate habit of getting caught in compromising situations (for which there is…