Movies Like Keeper of the Cup

If you liked Keeper of the Cup, a comedy movie directed by Jason Priestley, 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
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.
2
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.
3
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.
4
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.
5
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
6
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…
7
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.
8
Iliza Shlesinger: Freezing Hot (2015)
★ 6.7/10Also comedy
Smart and brazen comedian Iliza Shlesinger shares her unflinchingly honest observations on the differences between men and women. Filled with hashtag-able catch phrases, this is a laugh-out-loud revelation exposing…
9
Norm Macdonald: Me Doing Standup (2011)
★ 7.7/10Also comedy
Norm MacDonald, the iconic anchor of SNL's "Weekend Update" and star of the cult classic Dirty Work, is back with a vengeance.
10
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.
11
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
12
Dave Chappelle: The Closer (2021)
★ 7.2/10Also comedy
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.
13
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.
14
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.
15
High Anxiety (1977)
★ 6.4/10Also comedy
A psychiatrist with intense acrophobia (fear of heights) goes to work for a mental institution run by doctors who appear to be crazier than their patients, and have secrets that they are willing to commit murder to keep.
16
The F**k-It List (2020)
★ 6/10Also comedy
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
17
Jerry Seinfeld: I'm Telling You for the Last Time (1998)
★ 7.4/10Also comedy
Taped for HBO in August 1998, on the final date of Jerry Seinfeld's tour appearances at New York City's Broadhurst Theater, I'm Telling You for the Last Time presents the standup comedian's so-called "final" standup…
18
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.
19
Grown Ups (2010)
★ 6.4/10Also comedy
After their high school basketball coach passes away, five good friends and former teammates reunite for a Fourth of July holiday weekend.
20
Sarah Silverman: A Speck of Dust (2017)
★ 6.8/10Also comedy
In her first comedy special post-health scare, Sarah Silverman shares a mix of fun facts, sad truths and yeah-she-just-went-there moments.