Movies Like Hooligan in Jail

If you liked Hooligan in Jail (1903), a comedy movie, 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
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.
2
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
In 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.
3
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.
4
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
5
The F**k-It List (2020)
★ 6/10Also comedy
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
6
Trailer Park Boys: Don't Legalize It (2014)
★ 6.4/10Also comedy
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty…
7
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
8
Stir Crazy (1980)
★ 6.5/10Also comedy
New Yorkers Skip Donahue and Harry Monroe have no jobs and no prospects, so they decide to flee the city and find work elsewhere, landing jobs wearing woodpecker costumes to promote the opening of a bank. When their…
9
Don't Be a Menace to South Central While Drinking Your Juice in the Hood (1996)
★ 7/10Also comedy
When Ashtray moves to South Central L.A. to live with his father (who appears to be the same age he is) and grandmother (who likes to talk tough and smoke reefer), he falls in with his gang-banging cousin Loc Dog, who…
10
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.
11
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
12
Naked Gun 33⅓: The Final Insult (1994)
★ 6.5/10Also comedy
Frank Drebin is persuaded out of retirement to go undercover in a state prison. There he has to find out what top terrorist, Rocco, has planned for when he escapes. Adding to his problems, Frank's wife, Jane, is…
13
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
14
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
15
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.
16
The Hoose-Gow (1929)
★ 6.8/10Also comedy
Stan and Ollie arrive as new inmates at a prison after apparently taking part in a hold-up raid, a raid they tell a prison officer they were only watching. The usual mayhem ensues.
17
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.
18
Despicable Me 3 (2017)
★ 6.5/10Also comedy
Gru and his wife Lucy must stop former '80s child star Balthazar Bratt from achieving world domination.
19
Take the Money and Run (1969)
★ 7.1/10Also comedy
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
20
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…