Movies Like The Hustler of Money

If you liked The Hustler of Money (1987), a comedy movie directed by Ben Stiller and Ralph Glenn Howard, 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
UHF (1989)
★ 6.7/10Also comedy
The eccentric new manager of a UHF television channel tries to save the station from financial ruin with an odd array of programming.
2
And Now for Something Completely Different (1971)
★ 7.2/10Also comedy
A collection of Monty Python's Flying Circus skits from the first two seasons of their British TV series.
3
Happy Gilmore 2 (2025)
★ 6.5/10Also comedy
Happy Gilmore isn't done with golf — not by a long shot. Since his retirement after his first Tour Championship win, Gilmore returns to finance his daughter's ballet classes.
4
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
5
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.
6
Mystery Men (1999)
★ 5.9/10Also comedy
When Champion City's hero Captain Amazing is kidnapped by the recently paroled supervillain Casanova Frankenstein, a trio of average, everyday superheroes -- Mr. Furious, the Shoveler and the Blue Raja -- assemble a…
7
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
8
The Big Lebowski (1998)
★ 7.9/10Also comedy
Jeffrey 'The Dude' Lebowski, a Los Angeles slacker who only wants to bowl and drink White Russians, is mistaken for another Jeffrey Lebowski, a wheelchair-bound millionaire, and finds himself dragged into a strange…
9
Kevin Hart: I'm a Grown Little Man (2009)
★ 7.3/10Also comedy
Fresh off the heels of appearing in movies like Superhero Movie and The 40 Year-Old Virgin, fast-talking comedian Kevin Hart stars in this live stand-up performance where he makes fun of everything and everybody…
10
Hooper (1978)
★ 6.3/10Also comedy
Legendary stunt man Sonny Hooper remains one of the top men in his field, but due to too many stressful impacts to the spine and the need to pop painkillers several times a day, he knows he should get out of the…
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
The Roast of Tom Brady (2024)
★ 6.7/10Also comedy
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
13
Amazon Women on the Moon (1987)
★ 5.9/10Also comedy
Centered on a television station which features a 1950s-style sci-fi movie interspersed with a series of wild commercials, wacky shorts and weird specials, this lampoon of contemporary life and pop culture skewers some…
14
The Slammin' Salmon (2009)
★ 5.8/10Also comedy
The brutal former heavyweight boxing champion Cleon "Slammin'" Salmon (Duncan), now owner of a Miami restaurant, institutes a competition to see which waiter can earn the most money in one night: the winner stands to…
15
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
16
The Caddy (1953)
★ 6.4/10Also comedy
Although the son of a skilled golfer and an outstanding player in his own right, Harvey Miller is too nervous to play in front of a gallery, so he acts as coach and caddy for Joe Anthony, his girlfriend's brother.
17
Robot Chicken: Star Wars (2007)
★ 7.2/10Also comedy
A series of 30 sketches, following the hilarious antics of various characters from a galaxy, far, far away.
18
Donald's Golf Game (1938)
★ 6.2/10Also comedy
Donald Duck tries to exhibit his golfing ability to his nephews only to have them tease him with sneezes, noises and "trick" clubs. Finally, they put a grasshopper in a ball and it "jumps" all over.
19
Kingpin (1996)
★ 6.5/10Also comedy
After bowler Roy Munson swindles the wrong crowd and is left with a hook for a hand, he settles into impoverished obscurity. That is, until he uncovers the next big thing: an Amish kid named Ishmael. So, the corrupt…
20
The Art of Skiing (1941)
★ 7/10Also comedy
Goofy, staying at the Sugar Bowl resort, demonstrates the basics of downhill skiing, which the titles and announcer insist is pronounced "SHEEing". The equipment is, of course, of the era. As you can imagine, Goofy has…