Movies Like I'm a Juvenile Delinquent, Jail Me!

If you liked I'm a Juvenile Delinquent, Jail Me! (2004), a comedy and tv movie movie directed by Alex Cox, 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
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
2
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy and tv movie
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
3
How to Irritate People (1969)
★ 6.6/10Also comedy and tv movie
A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.
4
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
5
South Park (Not Suitable for Children) (2023)
★ 7.4/10Also comedy and tv movie
After it's discovered that a teacher at South Park Elementary has an OnlyFans page, Randy is compelled to take a closer look at the seedy underbelly of the world of online influencers.
6
The Big Bad Wolf (1934)
★ 6.5/10Also comedy
The Big Bad Wolf torments Little Red Riding Hood and the Three Little Pigs.
7
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy and tv movie
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.
8
Taylor Tomlinson: Look at You (2022)
★ 7.2/10Also comedy and tv movie
Breakups. Therapy. Bangs. Taylor's gone through some stuff since her quarter-life crisis, and she spins her mental health journey into insightful comedy.
9
Mike Birbiglia: Thank God for Jokes (2017)
★ 7.3/10Also comedy and tv movie
Mike Birbiglia declares that a joke should never end with "I’m joking." In his all-new comedy, Birbiglia tiptoes hilariously through the minefield that is modern-day joke-telling. Join Mike as he learns that the same…
10
Dave Chappelle: Sticks & Stones (2019)
★ 7.5/10Also comedy and tv movie
Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.
11
Dave Chappelle: The Closer (2021)
★ 7.2/10Also comedy and tv movie
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
12
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7/10Also comedy and tv movie
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…
13
The Drawn Together Movie: The Movie! (2010)
★ 6.4/10Also comedy
When the mystery-solving musician Foxxy Love notices she and her fellow housemates can curse without being bleeped—something they've never been able to do before—she realizes their show has been canceled. Determined to…
14
The Fixer Uppers (1935)
★ 6.8/10Also comedy
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
15
Clear History (2013)
★ 6.1/10Also comedy and tv movie
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
16
Robot Chicken: Star Wars (2007)
★ 7.2/10Also comedy
A series of 30 sketches, following the hilarious antics of various characters from a galaxy, far, far away.
17
Snoopy Presents: Welcome Home, Franklin (2024)
★ 7.7/10Also comedy
Franklin is new to town and hoping to make friends, but his usual tactics don't work on the Peanuts gang. When the Soap Box Derby arrives, he's sure it's a chance to impress new pals and teams up with the only other…
18
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
19
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.
20
Louis C.K.: Hilarious (2010)
★ 7.8/10Also comedy and tv movie
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.