Movies Like Jeff Ross Roasts Criminals: Live at Brazos County Jail

If you liked Jeff Ross Roasts Criminals: Live at Brazos County Jail (2015), 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
Comedy Central Roast of Justin Bieber (2015)
★ 6.8/10Also comedy
Several roasters, and the master himself Kevin Hart, make fun of Justin Bieber.
2
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.
3
Comedy Central Roast of James Franco (2013)
★ 7.2/10Also comedy
It's James Franco's turn to step in to the celebrity hot seat for the latest installment of The Comedy Central Roast.
4
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…
5
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…
6
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.
7
The Apple Dumpling Gang Rides Again (1979)
★ 6.4/10Also comedy
Amos and Theodore, the two bumbling outlaw wannabes from The Apple Dumpling Gang, are back and trying to make it on their own. This time, the crazy duo gets involved in an army supply theft case -- and, of course, gets…
8
Bandits (2001)
★ 6.3/10Also comedy
After escaping from prison, Joe and Terry go on a crime spree, robbing banks through Oregon and California in order to finance their scheme for a new life south of the border. Unfortunately, things get more complicated…
9
Comedy Central Roast of William Shatner (2006)
★ 6.5/10Also comedy
It's William Shatner's turn to step in to the celebrity hot seat for the latest installment of The Comedy Central Roast. A parade of Shatner's friends have gotten together to boldly go ...
10
Big Stan (2007)
★ 6.6/10Also comedy
A weak con man panics when he learns he's going to prison for fraud. He hires a mysterious martial arts guru who helps transform him into a martial arts expert who can fight off inmates who want to hurt or love him.
11
Money Talks (1997)
★ 6/10Also comedy
Sought by police and criminals, a small-time huckster makes a deal with a TV newsman for protection.
12
Half Baked (1998)
★ 6.3/10Also comedy
Three lovable party buds try to bail their friend out of jail. But just when the guys have mastered a plan, everything comes dangerously close to going up in smoke.
13
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…
14
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.
15
Desperate Living (1977)
★ 6.3/10Also comedy
After killing her husband, Peggy Gravel and her murderous maid Grizelda wind up in the crazy town of Mortville, where Queen Carlotta presides over a sleazy collection of misfits.
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
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.
18
We're No Angels (1955)
★ 7.2/10Also comedy
Three convicts escape from prison on Devil's Island just before Christmas and arrive at a nearby French colonial town. They go to the store of the Ducotels, the only store that gives supplies on credit. They initially…
19
Ocean's Eight (2018)
★ 6.9/10Also comedy
Debbie Ocean, a criminal mastermind, gathers a crew of female thieves to pull off the heist of the century at New York's annual Met Gala.
20
48 Hrs. (1982)
★ 6.7/10Also comedy
A hard-nosed cop reluctantly teams up with a wise-cracking criminal temporarily paroled to him, in order to track down a killer.