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Movies like Charlie on Parole (2009)

The best movies like Charlie on Parole (2009) are The F**k-It List (2020), Easy Money (1983) and Adventures in Public School (2018). If Charlie on Parole hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The F**k-It List (2020)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  2. Easy Money (1983)

    To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  3. 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

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  4. Anuvahood (2011)

    Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.

    Why it matches: Recommended by TMDB viewers · both comedy

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  5. Taking Care of Business (1990)

    An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. Dave Chappelle: The Unstoppable... (2025)

    Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.

    Why it matches: Recommended by TMDB viewers · both comedy

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  7. Ali Wong: Single Lady (2024)

    After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.

    Why it matches: Recommended by TMDB viewers · both comedy

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  8. Trailer Park Boys: Don't Legalize It (2014)

    Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty deal. Meanwhile, Ricky’s dope growing business is under a major threat when the government announces a plan to legalize marijuana. Bubbles reluctantly joins them on his own quest to claim an inheritance left to him by his long-lost parents.

    Why it matches: Recommended by TMDB viewers · both comedy

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  9. Bottle Rocket (1993)

    Dysfunctional friends Dignan and Anthony plan and execute a robbery with their pot-growing friend, Bob. The short film that inspired Wes Anderson’s feature debut.

    Why it matches: Recommended by TMDB viewers · both comedy

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  10. One Night at McCool's (2001)

    On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...

    Why it matches: Recommended by TMDB viewers · both comedy

  11. Me Time (2022)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

  12. Louis C.K.: Ridiculous (2026)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  13. Support Your Local Gunfighter (1971)

    A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.

    Why it matches: Recommended by TMDB viewers · both comedy

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  14. Why Worry? (1923)

    A hypochondriac vacations in the tropics for the fresh air - and finds himself in the middle of a revolution instead.

    Why it matches: Recommended by TMDB viewers · both comedy

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  15. Oscar (1991)

    Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets about to keep his promise.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Married to the Mob (1988)

    Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  17. The Best Man Holiday (2013)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

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  18. 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
  19. 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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  20. Ricky Gervais: Humanity (2018)

    In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this

Like Charlie on Parole and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Charlie on Parole?

The closest matches to Charlie on Parole are The F**k-It List (2020), Easy Money (1983) and Adventures in Public School (2018). Below are 17 more, each with the reason it matches.

What should I watch after Charlie on Parole?

Start with The F**k-It List (2020), the closest match to Charlie on Parole.

What is the highest-rated movie like Charlie on Parole?

Ricky Gervais: Humanity (2018), rated 7.6/10 by 547 TMDB users.

What is the newest movie like Charlie on Parole?

Louis C.K.: Ridiculous (2026) is the most recent release on this list.

Are there English movies like Charlie on Parole?

Yes: The F**k-It List (2020), Easy Money (1983) and Adventures in Public School (2018).

How are movies similar to Charlie on Parole chosen?

First come films that Trakt’s viewers watch alongside Charlie on Parole, 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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