Movies Like Tommy Boy

If you liked Tommy Boy (1995), a comedy movie directed by Peter Segal, 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
Dumb and Dumber (1994)
★ 6.7/10Also comedy
Lloyd and Harry are two men whose stupidity is really indescribable. When Mary, a beautiful woman, loses an important suitcase with money before she leaves for Aspen, the two friends (who have found the suitcase)…
2
Hollywood or Bust (1956)
★ 6.2/10Also comedy
The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the…
3
National Lampoon's Vacation (1983)
★ 7.1/10Also comedy
Clark Griswold is on a quest to take his family to the Walley World theme park for a vacation, but things don't go exactly as planned.
4
Planes, Trains and Automobiles (1987)
★ 7.3/10Also comedy
An irritable marketing executive, Neal Page, is heading home to Chicago for Thanksgiving when a number of delays force him to travel with a well meaning but overbearing shower curtain ring salesman, Del Griffith.
5
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.
6
The Odd Couple II (1998)
★ 6.3/10Also comedy
Brucey, the son of Oscar, calls his father to invite him to his wedding to Felix's daughter next Sunday in California. Oscar and Felix meet again at Los Angeles International Airport and rent a car in order to go to…
7
Wild Hogs (2007)
★ 6/10Also comedy
Restless and ready for an adventure, four suburban bikers leave the safety of their subdivision and head out on the open road. But complications ensue when they cross paths with an intimidating band of New Mexico…
8
Nothing to Lose (1997)
★ 6.6/10Also comedy
Advertising executive Nick Beame learns that his wife is sleeping with his employer. In a state of despair, he encounters a bumbling thief whose attempted carjacking goes awry when Nick takes him on an involuntary…
9
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
10
Disaster Holiday (2024)
★ 6.6/10Also comedy
A workaholic dad, trying to win over his kids, heads to the coast of Durban for a big work meeting — under the guise of a family road trip vacation.
11
Hot Shots! (1991)
★ 6.6/10Also comedy
The gang that created Airplane! and The Naked Gun sets its sights on Top Gun in this spoof. Topper Harley is a talented but unstable fighter pilot with an axe to grind: clearing the family name. His mission is to…
12
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.
13
The Family Plan (2023)
★ 7.2/10Also comedy
Dan Morgan is many things: a devoted husband, a loving father, a celebrated car salesman. He's also a former assassin. And when his past catches up to his present, he's forced to take his unsuspecting family on a road…
14
Nirvanna the Band the Show the Movie (2026)
★ 7.6/10Also comedy
When their plan to book a show at the Rivoli goes horribly wrong, Matt and Jay accidentally travel back to the year 2008.
15
Big Trouble (2002)
★ 6.1/10Also comedy
The story of how a mysterious suitcase brings together, and changes, the lives of a divorced dad, an unhappy housewife, two hitmen, a pair of street thugs, two love struck teens, two FBI men and a psychedelic toad…
16
Batman and Harley Quinn (2017)
★ 6.2/10Also comedy
Batman and Nightwing are forced to team with the Joker's sometimes-girlfriend Harley Quinn to stop a global threat brought about by Poison Ivy and Jason Woodrue, the Floronic Man.
17
Ride Along 2 (2016)
★ 6.3/10Also comedy
As his wedding day approaches, Ben heads to Miami with his soon-to-be brother-in-law James to bring down a drug dealer who's supplying the dealers of Atlanta with product.
18
Playdate (2025)
★ 6.2/10Also comedy
When out-of-work accountant Brian joins stay-at-home dad Jeff for a playdate with their sons, he expects a laid-back afternoon. Instead, they're chased by mercenaries, and Brian—totally unprepared—must survive one…
19
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.
20
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10Also comedy
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…