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Movies like Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head (1999)

The best movies like Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head (1999) are Held Up (1999), Sextuplets (2019) and Driver's Ed (2026). If Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Held Up (1999)

    What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.

    Why it matches: Recommended by TMDB viewers · both comedy

  2. Sextuplets (2019)

    Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  3. Driver's Ed (2026)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. No Time for Sergeants (1958)

    Georgia farm boy Will Stockdale is about to bust with pride. He’s been drafted. Will’s ready. But is Uncle Sam ready for Will?

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  5. Eenie Meanie (2025)

    A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  6. Fun with Dick and Jane (1977)

    When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  7. 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

    Popcorn FlickMovies like this
  8. Ricky Gervais: Mortality (2025)

    Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  9. Babes (2024)

    After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  10. 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
  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. 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

    Popcorn FlickMovies like this
  13. Ricky Gervais: Armageddon (2023)

    Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  14. Louis C.K.: Oh My God (2013)

    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 writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  15. Wet Hot American Summer (2001)

    It's the last day of Camp Firewood's season, but there's still time for the big talent show, a little romance… and for everyone to be wiped out by the piece of NASA's Skylab that's hurtling toward Earth.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. LaRoy, Texas (2024)

    Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  17. 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

    Popcorn FlickMovies like this
  18. 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

    Popcorn FlickMovies like this
  19. 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

    Popcorn FlickMovies like this
  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 Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head and something else?

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

Frequently asked questions

What are the best movies like Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head?

The closest matches to Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head are Held Up (1999), Sextuplets (2019) and Driver's Ed (2026). Below are 17 more, each with the reason it matches.

What should I watch after Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head?

Start with Held Up (1999), the closest match to Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head.

What is the highest-rated movie like Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head?

Louis C.K.: Oh My God (2013), rated 7.6/10 by 229 TMDB users.

What is the newest movie like Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head?

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

Are there English movies like Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head?

Yes: Held Up (1999), Sextuplets (2019) and Driver's Ed (2026).

How are movies similar to Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head chosen?

First come films that Trakt’s viewers watch alongside Long Strange Trip, or The Writer, the Naked Girl, and the Guy with a Hole in His Head, 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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