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Movies like The Cheekiest Man on Earth (1908)

The best movies like The Cheekiest Man on Earth (1908) are Dave Chappelle: The Dreamer (2023), Chris Rock: Selective Outrage (2023) and Mr. Bones (2001). If The Cheekiest Man on Earth hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Dave Chappelle: The Dreamer (2023)

    From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.

    Why it matches: Recommended by TMDB viewers · both comedy

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  2. Chris Rock: Selective Outrage (2023)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  3. Mr. Bones (2001)

    A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.

    Why it matches: Recommended by TMDB viewers · both comedy

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  4. Hannibal Buress: Comedy Camisado (2016)

    He's a kamikaze gambler. A one-arm cuddler. And if his fly is down, so be it. A night of sly riffs and slow burns.

    Why it matches: Recommended by TMDB viewers · both comedy

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  5. Thunderstruck (2012)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. Pups Alone (2021)

    After receiving an exciting new job opportunity at a cutting edge Pet Invention company, Robert, his teenage daughter Jenna and their trusty and special border collie Charlie make the move to the new neighborhood, right before Christmas. Upon arriving, Robert meets his gorgeous next door neighbor Holly, and her sassy and spunky border collie Gidget. Before the sparks can fly, they are set upon my Robert’s conniving and obnoxious next door neighbor and project manager Victor, his neighborhood bully bulldog “Vinnie P” and the sycophantic sidekick Chihuahua “Jose”.

    Why it matches: Recommended by TMDB viewers · both comedy

  7. Chris Rock: Kill the Messenger (2008)

    An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  8. 2 Minutes of Fame (2020)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  9. Jerry Seinfeld: 23 Hours to Kill (2020)

    Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.

    Why it matches: Recommended by TMDB viewers · both comedy

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  10. Shane Gillis: Beautiful Dogs (2023)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  11. 29th Street (1991)

    After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.

    Why it matches: Recommended by TMDB viewers · both comedy

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  12. The Roast of Tom Brady (2024)

    Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. The Horse's Mouth (1958)

    Gulley Jimson is a boorish aging artist recently released from prison. A swindler in search of his next art project, he hunkers down in the penthouse of would-be patrons the Beeders while they go on an extended vacation; he paints a mural on their wall, pawns their valuables and, along with the sculptor Abel, inadvertently smashes a large hole in their floor. Jimson's next project is an even larger wall in an abandoned church.

    Why it matches: Recommended by TMDB viewers · both comedy

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  14. Comedy Central Roast of Justin Bieber (2015)

    Several roasters, and the master himself Kevin Hart, make fun of Justin Bieber.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. Accident Man (2018)

    Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Pretty Persuasion (2005)

    A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.

    Why it matches: Recommended by TMDB viewers · both comedy

  17. The Wonderful World of Mickey Mouse: Steamboat Silly (2023)

    Mickey and gang must stop hundreds of old film reel versions of Mickey from wreaking havoc all over town.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. Wrong Cops (2013)

    A group of bad cops look to dispose of a body that one of them accidentally shot.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Good Neighbor Sam (1964)

    To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral appearance.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. Adventures in Public School (2018)

    A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this

Like The Cheekiest Man on Earth and something else?

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Frequently asked questions

What are the best movies like The Cheekiest Man on Earth?

The closest matches to The Cheekiest Man on Earth are Dave Chappelle: The Dreamer (2023), Chris Rock: Selective Outrage (2023) and Mr. Bones (2001). Below are 17 more, each with the reason it matches.

What should I watch after The Cheekiest Man on Earth?

Start with Dave Chappelle: The Dreamer (2023), the closest match to The Cheekiest Man on Earth.

What is the highest-rated movie like The Cheekiest Man on Earth?

Accident Man (2018), rated 6.3/10 by 633 TMDB users.

What is the newest movie like The Cheekiest Man on Earth?

The Roast of Tom Brady (2024) is the most recent release on this list.

Are there English movies like The Cheekiest Man on Earth?

Yes: Dave Chappelle: The Dreamer (2023), Chris Rock: Selective Outrage (2023) and Mr. Bones (2001).

How are movies similar to The Cheekiest Man on Earth chosen?

First come films that Trakt’s viewers watch alongside The Cheekiest Man on Earth, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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