Movies Like Grandma's Boy

If you liked Grandma's Boy (2006), a comedy movie directed by Nicholaus Goossen, 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
Grudge Match (2013)
★ 6.1/10Also comedy
A pair of aging boxing rivals are coaxed out of retirement to fight one final bout -- 30 years after their last match.
2
Greedy (1994)
★ 6.2/10Also comedy
Meet the McTeagues. They've come to stake a claim in their wealthy uncle's will… only he's not dead yet!
3
Dungeons & Dragons: Honor Among Thieves (2023)
★ 7.4/10Also comedy
A charming thief and a band of unlikely adventurers undertake an epic heist to retrieve a lost relic, but things go dangerously awry when they run afoul of the wrong people.
4
How High 2 (2019)
★ 6.2/10Also comedy
When two jobless friends discover a hidden weed bible and the ultimate bud, they think that they’ve got it made…with 'seed' money to start a new snack delivery app. But, when nearly all of their stash and weed bible…
5
Your Sister's Sister (2011)
★ 6.5/10Also comedy
Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks off a revealing stretch of days.
6
The Simpsons: O C'mon All Ye Faithful (2024)
★ 7/10Also comedy
The residents of Springfield search for Christmas cheer.
7
The Great Outdoors (1988)
★ 6.5/10Also comedy
It's vacation time for outdoorsy Chicago man Chet Ripley, along with his wife, Connie, and their two kids, Buck and Ben. But a serene weekend of fishing at a Wisconsin lakeside cabin gets crashed by Connie's obnoxious…
8
Happy Gilmore (1996)
★ 6.7/10Also comedy
Failed hockey player-turned-golf whiz Happy Gilmore — whose unconventional approach and antics on the green courts the ire of rival Shooter McGavin — is determined to win a PGA tournament so he can save his granny's…
9
Easy Money (1983)
★ 6/10Also comedy
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
10
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
11
Kung Pow: Enter the Fist (2002)
★ 6.6/10Also comedy
A movie within a movie, created to spoof the martial arts genre. Writer/director Steve Oedekerk uses contemporary characters and splices them into a 1970s kung-fu film, weaving the new and old together. As the main…
12
Addams Family Values (1993)
★ 7/10Also comedy
Siblings Wednesday and Pugsley Addams will stop at nothing to get rid of Pubert, the new baby boy adored by parents Gomez and Morticia. Things go from bad to worse when the new "black widow" nanny, Debbie Jellinsky…
13
The Warriors Gate (2016)
★ 6.6/10Also comedy
After a mysterious chest opens a gateway through time, teen gamer Jack is transported to an ancient empire terrorized by a cruel barbarian king. Jack will need all of his gaming skills as he battles to defeat the…
14
McLintock! (1963)
★ 6.6/10Also comedy
Aging rancher and self-made man, George Washington McLintock is forced to deal with numerous personal and professional problems. Seemingly everyone wants a piece of his enormous farmstead, including high-ranking…
15
Horrible Bosses 2 (2014)
★ 6.2/10Also comedy
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
16
National Lampoon's Loaded Weapon 1 (1993)
★ 6.1/10Also comedy
An LA detective is murdered because she has microfilm with the recipe to make cocaine cookies. Two cops partner to find and stop the fiends before they can dope the nation by distributing their wares via the…
17
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!
18
Last Vegas (2013)
★ 6.4/10Also comedy
Aging pals Billy, Paddy, Archie, and Sam have been best friends since childhood. When Billy finally proposes to his much-younger girlfriend, all four friends go to Las Vegas to celebrate the end of Billy's longtime…
19
My Spy (2020)
★ 6.9/10Also comedy
A hardened CIA operative finds himself at the mercy of a precocious 9-year-old girl, having been sent undercover to surveil her family.
20
Out Cold (2001)
★ 5.9/10Also comedy
Rick Rambis and his friends are having the time of their lives on Bull Mountain—until the legendary Papa Muntz' son decides to sell the mountain to a sleazy land developer, have the staff fired and turn Bull Mountain…