Movies Like Heads I Win, Tails You Lose

If you liked Heads I Win, Tails You Lose (1982), a comedy movie directed by Nanni Loy, 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
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…
2
Goodnight, Ladies and Gentlemen (1976)
★ 6.7/10Also comedy
An episodic satire of the political and social status of Italy in the seventies, through the shows of one day of a television channel.
3
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…
4
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.
5
The Trouble with Angels (1966)
★ 6.7/10Also comedy
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
6
The Most Beautiful Day in the World (2019)
★ 6/10Also comedy
Arturo Meraviglia is a struggling impresario who has to take care of Gioele and Rebecca, two children "inherited" by an old uncle. When he realizes that little Gioele has superpowers, his luck changes.
7
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.
8
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…
9
The Marquis of Grillo (1981)
★ 7.8/10Also comedy
In 18th-century Rome, impish aristocrat Onofrio del Grillo amuses himself by playing pranks on all sorts of people — his reactionary family and fellow nobles, the poors, the French occupiers trying to modernize…
10
Fantozzi (1975)
★ 7.8/10Also comedy
A good-natured but unlucky Italian is constantly finding himself in difficult situations, but never losing his mood.
11
Adventures in Public School (2018)
★ 6.3/10Also comedy
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
12
Love & Slaps (2010)
★ 6.1/10Also comedy
A comedy about generational conflict between two parents who do not want to grow old and a seventeen year old daughter who wants to become an adult. During a weekend with some friends in their country house in Tuscany…
13
Occhio, malocchio, prezzemolo e finocchio (1983)
★ 5.9/10Also comedy
The film is divided into two episodes, The Hair of Disgrace and The Magician, both focusing on the theme of the occult and beliefs. The title translates as "Eye, Evil Eye, Parsley and Fennel".
14
The Con Artists (1976)
★ 7.1/10Also comedy
Belle Duke, in order to get revenge on her former lover Philip Bang, organizes his jail break. But instead of Philip, it is the Italian Felice Brianza, AKAS Felix, who escapes. Now Felix is obliged to help Philip to…
15
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
16
Fantozzi Still Suffers (1983)
★ 6.5/10Also comedy
After a hard day at work and a condominium-board meeting, accountant Ugo Fantozzi goes on a trip with his family. Unfortunately, he will face a nasty surprise upon his return.
17
Ho visto le stelle (2003)
★ 5.9/10Also comedy
The young Antonio wants to participate in a reality show and leaves Naples for Milan with his best friend Eugenio.
18
Boris: The Film (2011)
★ 6.9/10Also comedy
A director and his crew attempt to make the transition from the small to the big screen.
19
Grand Hotel Excelsior (1982)
★ 6.1/10Also comedy
Taddeus is the manager of the Grand Hotel Excelsior. The Summer season begins in May and since then many odd persons frequent the hotel. There is Ilde Vivaldi, in love with Taddeus and the boxer Pericle Coccia who has…
20
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!