Movies Like Cupid Aims High

If you liked Cupid Aims High (1990), a comedy movie directed by Marjo Valve, 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
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.
2
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.
3
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
4
Gabriel Iglesias: Hot and Fluffy (2007)
★ 7.6/10Also comedy
Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now…
5
Amy Schumer: Mostly Sex Stuff (2012)
★ 5.9/10Also comedy
A ratings hit! Amy Schumer debuts her one-hour special in front of a live audience at the Historic Fillmore Theatre in San Francisco. Nothing is off limits as Schumer airs every hilarious, messed up detail of her…
6
Ray Romano: Right Here, Around the Corner (2019)
★ 6.8/10Also comedy
Ray Romano first cut his stand-up teeth at the Comedy Cellar in New York. Now, in his first comedy special in 23 years, he returns to where it all began.
7
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
8
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
9
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…
10
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
11
Rowan Atkinson Live (1992)
★ 8.2/10Also comedy
Rowan Atkinson and Angus Deayton in Boston doing a live performance of the same styles of humor we've seen in Mr. Bean and Blackadder. Included are lessons on Shakespearean acting, a school headmaster meeting with the…
12
For the Matches (1980)
★ 6.3/10Also comedy
In Eastern Finland, in Liperi to be exact, Anna-Liisa Ihalainen asks her husband Antti to get some matches from the Ihalainen household. Unfortunately that trip takes a little longer than expected...
13
Dave Chappelle: The Bird Revelation (2017)
★ 7.5/10Also comedy
Comedy juggernaut Dave Chappelle's fourth Netflix Special, taped on November 20th, 2017 at Los Angeles' Comedy Store.
14
Dog Gone (2008)
★ 6.5/10Also comedy
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
15
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.
16
The Geisha Boy (1958)
★ 6.4/10Also comedy
Gilbert Wooley is a second-rate magician who is sent to entertain the troops in the pacific. During his time in Japan he becomes attached to a little orphan boy.
17
Pups Alone (2021)
★ 5.8/10Also comedy
After receiving an exciting new job opportunity at a cutting edge Pet Invention company, Robert, his teenage daughter Jenna and their trusty and special border collie Charlie make the move to the new neighborhood…
18
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
19
Wake Up, Ron Burgundy: The Lost Movie (2004)
★ 6/10Also comedy
While Ron Burgundy's rivalry with Veronica Corningstone escalates quickly, a group of unprofessional thieves better known as 'The Alarm Clock' try to make the truth known, whatever that may mean...
20
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.