Movies Like Cleo/Leo

If you liked Cleo/Leo (1989), a comedy and fantasy movie directed by Chuck Vincent, 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
Ladies First (2026)
★ 6/10Also comedy and fantasy
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.
2
Caught Stealing (2025)
★ 6.8/10Also comedy
Burned-out ex-baseball player Hank Thompson unexpectedly finds himself embroiled in a dangerous struggle for survival amidst the criminal underbelly of late 1990s New York City, forced to navigate a treacherous…
3
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.
4
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.
5
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…
6
The Hot Chick (2002)
★ 6.4/10Also comedy and fantasy
Not only is Jessica Spencer the most popular girl in school -- she is also the meanest. But things change for the attractive teen when a freak accident involving a cursed pair of earrings and a chance encounter at a…
7
The Wrong Guy (1997)
★ 6.8/10Also comedy
Nelson Hibbert expects to become the new president of Nagel Industries, but Mr. Nagel gives the promotion to another employee. When Nelson barges into Nagel's office to confront him, he finds Nagel's been murdered…
8
Dream Scenario (2023)
★ 6.6/10Also comedy and fantasy
Hapless family man Paul Matthews finds his life turned upside down when millions of strangers suddenly start seeing him in their dreams. But when his nighttime appearances take a nightmarish turn, Paul is forced to…
9
Jawbreaker (1999)
★ 6.4/10Also comedy
When an exclusive clique of teenage socialites accidentally murder their best friend on the morning of her birthday, the three girls responsible conspire to hide the truth.
10
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…
11
Beau Is Afraid (2023)
★ 6.7/10Also comedy and fantasy
Following the sudden death of his mother, a mild-mannered but anxiety-ridden man confronts his darkest fears as he embarks on an epic odyssey back home.
12
Into the Night (1985)
★ 6.5/10Also comedy
Ed Okin used to have a boring life. He used to have trouble getting to sleep. Then one night, he met Diana. Now, Ed's having trouble staying alive.
13
It's What's Inside (2024)
★ 6.5/10Also comedy
A pre-wedding reunion descends into a psychological nightmare for a group of college friends when a surprise guest arrives with a mysterious suitcase.
14
Freaky Tales (2025)
★ 6.3/10Also comedy
In 1987 Oakland, a mysterious force guides The Town's underdogs in four interconnected tales: teen punks defend their turf against Nazi skinheads, a rap duo battles for hip-hop immortality, a weary henchman gets a shot…
15
Dogma (1999)
★ 6.9/10Also fantasy and comedy
An abortion clinic worker with a special heritage is called upon to save the existence of humanity from being negated by two renegade angels trying to exploit a loophole and re-enter Heaven.
16
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.
17
See No Evil, Hear No Evil (1989)
★ 6.8/10Also comedy
A murder takes place in the shop of David Lyons, a deaf man who fails to hear the gunshot being fired. Outside, blind man Wally Karue hears the shot, but cannot see the perpetrator. Both are arrested, but escape to…
18
How High (2001)
★ 6.4/10Also comedy
Jamal and Silas, two ordinary guys who smoke something magical, pass their college entrance exams with flying colors and end up at Harvard. Ivy League ways are strange but Silas and Jamal take it in a stride -- until…
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
Desperately Seeking Susan (1985)
★ 6.1/10Also comedy
A bored New Jersey suburban housewife's fascination with a free-spirited woman she has read about in the personal columns leads to her being mistaken for the woman herself and into a chaotic adventure of amnesia and…