Movies Like Looking for Trouble

If you liked Looking for Trouble (1919), a comedy movie directed by Hal Roach, 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
Good Neighbor Sam (1964)
★ 6.6/10Also comedy
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral…
2
The Champion (1915)
★ 6.5/10Also comedy
Walking along with his bulldog, Charlie finds a "good luck" horseshoe just as he passes a training camp advertising for a boxing partner "who can take a beating." After watching others lose, Charlie puts the horseshoe…
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
The Distinguished Gentleman (1992)
★ 6/10Also comedy
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
5
2 Minutes of Fame (2020)
★ 6.6/10Also comedy
An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.
6
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.
7
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…
8
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…
9
Down and Out in Beverly Hills (1986)
★ 5.9/10Also comedy
Beverly Hills couple Barbara and Dave Whiteman find their lives altered by the arrival of a vagrant who tries to drown himself in their swimming pool.
10
Eddie Izzard: Dress to Kill (1999)
★ 7.8/10Also comedy
Eddie 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…
11
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.
12
Snatch (2000)
★ 7.8/10Also comedy
Unscrupulous boxing promoters, violent bookies, a Russian gangster, incompetent amateur robbers, and supposedly Jewish jewellers fight to track down a priceless stolen diamond.
13
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed 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…
14
Die Hart (2023)
★ 5.9/10Also comedy
Kevin Hart - playing a version of himself - is on a death-defying quest to become an action star. And with a little help from John Travolta, Nathalie Emmanuel, and Josh Hartnett - he just might pull it off.
15
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
16
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedy
From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.
17
The Wedding Ringer (2015)
★ 6.5/10Also comedy
Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO…
18
Support Your Local Gunfighter (1971)
★ 6.6/10Also comedy
A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.
19
Back to the Beach (1987)
★ 5.9/10Also comedy
A former beach boy and his wife go to California to visit their daughter and become part of the new beach scene.
20
Ladies First (2026)
★ 6/10Also comedy
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.