Movies Like Jolly: A Life

If you liked Jolly: A Life (1995), a comedy movie directed by Ron Bain, here are 19 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
The Geisha Boy (1958)
★ 6.5/10Also comedy
Gilbert Wooley is a second-rate magician who is sent to entertain the troops in the pacific. During his time in Japan he becomes attached to a little orphan boy.
3
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
4
Ali G, Innit (1999)
★ 6.5/10Also comedy
Ali G travels throughout Britain, interviewing unsuspecting leaders and politicians.
5
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.
6
My Spy (2020)
★ 6.9/10Also comedy
A hardened CIA operative finds himself at the mercy of a precocious 9-year-old girl, having been sent undercover to surveil her family.
7
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
8
Playing with Fire (2019)
★ 6.6/10Also comedy
A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.
9
Clear History (2013)
★ 6.1/10Also comedy
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.
10
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.
11
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.
12
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
13
Chris Rock: Never Scared (2004)
★ 7.5/10Also comedy
Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful…
14
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.
15
The Best Man Holiday (2013)
★ 6.5/10Also comedy
When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.
16
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.
17
A Bad Moms Christmas (2017)
★ 6.3/10Also comedy
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
18
Trouble Man (2025)
★ 7/10Also comedy
Jaxen, a former cop turned Atlanta PI, is hired to find missing R&B star Jahari. His investigation uncovers her disappearance is connected to a larger conspiracy, forcing him to question those around him and his own…
19
Three O'Clock High (1987)
★ 6.8/10Also comedy
Nerdy high schooler Jerry Mitchell is assigned to write an article for the school paper about the infamous new delinquent transfer student, Buddy Revell. When Jerry accidentally invades Buddy's personal space and…