Movies Like Paul F. Tompkins: You Should Have Told Me

If you liked Paul F. Tompkins: You Should Have Told Me (2010), a comedy movie directed by Neil Mahoney, 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
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.
2
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
3
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.
4
Chris Rock: Selective Outrage (2023)
★ 6.2/10Also comedy
Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.
5
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.
6
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
7
Anthony Jeselnik: Bones and All (2024)
★ 7.1/10Also comedy
Anthony Jeselnik celebrates 20 years of delivering boundary-pushing comedy to the masses in this razor-sharp stand-up special.
8
Dave Chappelle: The Unstoppable... (2025)
★ 6.7/10Also comedy
Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.
9
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.
10
Ricky Gervais: Humanity (2018)
★ 7.7/10Also comedy
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
11
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.
12
2 Minutes of Fame (2020)
★ 6.6/10Also comedy
An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.
13
Eddie Murphy: Delirious (1983)
★ 7.6/10Also comedy
Taped live and in concert at Constitution Hall in Washington, D.C. in August, 1983, Eddie Murphy: Delirious captures Eddie Murphy's wild and outrageous stand-up comedy act, which he performed in New York and eighteen…
14
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
15
Adventures in Public School (2018)
★ 6.3/10Also comedy
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
16
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…
17
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.
18
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.
19
Iliza Shlesinger: War Paint (2013)
★ 6.5/10Also comedy
Her innocent appearance is just a cover for Last Comic Standing winner Iliza Shlesinger's acerbic, stream-of-conscious comedy that she unleashes on an unsuspecting audience in her hometown of Dallas in "War Paint," her…
20
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…