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Movies like Why Men Are Clueless (2019)

The best movies like Why Men Are Clueless (2019) are Bill Burr: Drop Dead Years (2025), Iliza Shlesinger: Freezing Hot (2015) and Adam Sandler: Love You (2024). If Why Men Are Clueless hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Bill Burr: Drop Dead Years (2025)

    In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  2. Iliza Shlesinger: Freezing Hot (2015)

    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 some of women’s best kept - and ugliest - secrets, including truths about first date attire, fantasy break-ups and the tireless pursuit of not being cold while still looking hot.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  3. Adam Sandler: Love You (2024)

    Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. 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
  5. 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
  6. Dave Chappelle: The Closer (2021)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  7. John Mulaney: Kid Gorgeous at Radio City (2018)

    John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Absolute CinemaMovies like this
  8. 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
  9. Louis C.K.: Hilarious (2010)

    In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  10. Chris Rock: Tamborine (2018)

    Chris Rock takes the stage for his first comedy special in 10 years, filled with searing observations on fatherhood, infidelity and American politics.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  11. Dylan Moran: Like, Totally (2006)

    Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  12. 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
  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. The Wedding Year (2019)

    A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

    Why it matches: Recommended by TMDB viewers · both comedy

  15. Taylor Tomlinson: Have It All (2024)

    Can Taylor Tomlinson have it all? From dating woes to dream jobs to inventive dirty talk, she shares life's ups and downs in this stand-up comedy special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Iliza Shlesinger: War Paint (2013)

    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 first stand-up special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  17. Eddie Murphy Raw (1987)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  18. 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
  19. Dave Chappelle: Sticks & Stones (2019)

    Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  20. 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

    Popcorn FlickMovies like this

Like Why Men Are Clueless and something else?

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Frequently asked questions

What are the best movies like Why Men Are Clueless?

The closest matches to Why Men Are Clueless are Bill Burr: Drop Dead Years (2025), Iliza Shlesinger: Freezing Hot (2015) and Adam Sandler: Love You (2024). Below are 17 more, each with the reason it matches.

What should I watch after Why Men Are Clueless?

Start with Bill Burr: Drop Dead Years (2025), the closest match to Why Men Are Clueless.

What is the highest-rated movie like Why Men Are Clueless?

John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.

What is the newest movie like Why Men Are Clueless?

Driver's Ed (2026) is the most recent release on this list.

Are there English movies like Why Men Are Clueless?

Yes: Bill Burr: Drop Dead Years (2025), Iliza Shlesinger: Freezing Hot (2015) and Adam Sandler: Love You (2024).

How are movies similar to Why Men Are Clueless chosen?

First come films that Trakt’s viewers watch alongside Why Men Are Clueless, 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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