Movies Like Safe in Jail

If you liked Safe in Jail (1913), a comedy movie directed by Mack Sennett, 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
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.
2
YES DAY (2021)
★ 6.7/10Also comedy
A mom and dad who usually say no decide to say yes to their kids' wildest requests — with a few ground rules — on a whirlwind day of fun and adventure.
3
Destry Rides Again (1939)
★ 7.2/10Also comedy
Tom Destry, son of a legendary frontier peacekeeper, doesn’t believe in gunplay. Thus he becomes the object of widespread ridicule when he rides into the wide-open town of Bottleneck, the personal fiefdom of the…
4
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.
5
Laughing Gravy (1931)
★ 7.2/10Also comedy
Stan and Ollie try to hide their pet dog Laughing Gravy from their exasperated, mean tempered landlord, who has a "No Pets" policy.
6
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
7
Pardon Us (1931)
★ 6.4/10Also comedy
It's Prohibition, and the boys wind up behind bars after Stan sells some of their home-brew beer to a policeman.
8
Malibu Rescue: The Next Wave (2020)
★ 6.2/10Also comedy
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on…
9
Two-Way Stretch (1960)
★ 6.7/10Also comedy
Three criminals plan to break out of prison the day before their release in order to carry out a daring jewel robbery, intending to establish the perfect alibi by returning to jail afterwards. First however they must…
10
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…
11
Playing with Fire (2019)
★ 6.6/10Also comedy
A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.
12
The Air Up There (1994)
★ 6.1/10Also comedy
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home…
13
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.
14
Wrong Cops (2013)
★ 6.1/10Also comedy
A group of bad cops look to dispose of a body that one of them accidentally shot.
15
Dog Gone (2008)
★ 6.5/10Also comedy
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
16
Rock-a-Bye Baby (1958)
★ 6.9/10Also comedy
An average television repairman must care for the newborn triplets of his former hometown sweetheart—now a famous movie star—so her career will not suffer.
17
Welcome to Collinwood (2002)
★ 6.1/10Also comedy
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
18
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…
19
Song of the Thin Man (1947)
★ 6.7/10Also comedy
While attending a glamorous jazz cruise on New York’s East River, Nick and Nora Charles witness the fatal shooting of a wealthy patron. When suspicion falls on a young bandleader and his musicians, the couple steps in…
20
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.