Movies Like My Boss Was a Fool
If you liked My Boss Was a Fool (1969), a comedy movie directed by Errikos Thalassinos, 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
Much Ado About Nothing (2013)
★ 6.8/10Also comedyA modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
- 2
Me Time (2022)
★ 5.8/10Also comedyWith his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
- 3
Driver's Ed (2026)
★ 6.9/10Also comedyA 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.
- 4
Fun with Dick and Jane (1977)
★ 6.6/10Also comedyWhen an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
- 5
The Wedding Year (2019)
★ 5.9/10Also comedyA commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
- 6
Like a Boss (2020)
★ 6.2/10Also comedyTwo female friends with very different ideals decide to start a beauty company together. One is more practical, while the other wants to earn her fortune and live a lavish lifestyle.
- 7
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedyHawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
- 8
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedyIn what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
- 9
Eddie Izzard: Dress to Kill (1999)
★ 7.8/10Also comedyEddie Izzard takes her show to San Francisco to give a brief history of pagan and Christian religions, the building of Stonehenge, the birth of the Church of England and of Western empires, and the need for a European…
- 10
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedyUnbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
- 11
Beau Hunks (1931)
★ 6.8/10Also comedyStan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
- 12
Duplex (2003)
★ 6.1/10Also comedyWhen a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
- 13
72 HOURS (2026)
★ 6.8/10Also comedyTo save his career, a 40-year-old ad exec joins a crew of twentysomethings for a wild Miami bachelor party after they mistakenly add him to a group chat.
- 14
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedyFilmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…
- 15
Tommy Boy (1995)
★ 6.8/10Also comedyTo save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
- 16
Jim Jefferies: Intolerant (2020)
★ 7.1/10Also comedyBetween scenes from an excruciating date, Jim Jefferies digs into generational differences, his own bad habits and the shifting boundaries in comedy.
- 17
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedyIn 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.
- 18
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
- 19
Eddie Murphy Raw (1987)
★ 7.2/10Also comedyEddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
- 20
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedyFrom his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.