Movies Like See You in Jail

If you liked See You in Jail (1927), a comedy movie directed by Joseph Henabery, 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
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
2
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.
3
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
4
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.
5
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.
6
Eddie Murphy Raw (1987)
★ 7.2/10Also comedy
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
7
Die, Mommie, Die! (2003)
★ 6.6/10Also comedy
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her…
8
My Wife's Relations (1922)
★ 6.2/10Also comedy
Buster and a woman are mistakenly married and her initially unfriendly family begins to treat him nicely when they come to believe he has a large inheritance awaiting him.
9
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.
10
Confess, Fletch (2022)
★ 6.2/10Also comedy
The roguishly charming and endlessly troublesome Fletch becomes the prime suspect in a murder case while searching for a stolen art collection. The only way to prove his innocence? Find out which of the long list of…
11
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
12
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
13
A Burlesque on Carmen (1915)
★ 5.8/10Also comedy
A gypsy seductress is sent to sway a goofy officer to allow a smuggling run.
14
The Twelve Chairs (1970)
★ 6.2/10Also comedy
In 1920s Soviet Russia, a fallen aristocrat, a priest and a con artist search for a treasure of jewels hidden inside one of twelve dining chairs, lost during the revolution.
15
A Woman (1915)
★ 6.1/10Also comedy
Mother, father and daughter go to the park. The women doze off on a bench while the father plays a hide-and-seek game with a girl, blindfolded. Charlie leads him into a lake. Both dozing ladies on the bench fall for…
16
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.
17
Cars Toon Mater's Tall Tales (2008)
★ 7.1/10Also comedy
Mater the tow truck travels from country to country as he retells his infamous but unbelievable stories.
18
Hard Luck (1921)
★ 6.9/10Also comedy
A down on his luck young man makes several attempts at committing suicide but fails them too. He then finds himself becoming more confident through a series of petty adventures, to such an extent that this becomes his…
19
Eenie Meanie (2025)
★ 6.3/10Also comedy
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
20
Jim Jefferies: This Is Me Now (2018)
★ 7/10Also comedy
The gleefully irreverent Jefferies skewers “grabby” celebrities, political hypocrisy and his own ill-advised career moves in a brash stand-up special.