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Movies like Confessions of a Womanizer (2014)

The best movies like Confessions of a Womanizer (2014) are The F**k-It List (2020), Spa Weekend (2026) and Held Up (1999). If Confessions of a Womanizer 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. Spa Weekend (2026)

    Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break, the women escape to a luxury spa retreat for an unforgettable weekend dedicated to fun, laughter, and a lot of really bad decisions.

    Why it matches: Recommended by TMDB viewers · both comedy

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  3. 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

  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. 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
  6. 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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  7. 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

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  8. Russell Peters: Almost Famous (2016)

    The comic comes home to Toronto to sound off on cultural quirks, furniture building and bathroom visits, revelling in all things ridiculously human.

    Why it matches: Recommended by TMDB viewers · both comedy

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  9. Nikki Glaser: Someday You'll Die (2024)

    Comedian and actress Nikki Glaser is back in her second HBO special, diving into a wide range of topics including why she doesn't want kids, the harsh realities of aging, her sexual fantasies and more.

    Why it matches: Recommended by TMDB viewers · both comedy

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  10. 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
  11. 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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  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

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  13. 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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  14. American Dreamer (2022)

    In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.

    Why it matches: Recommended by TMDB viewers · both comedy

  15. 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

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  16. 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

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  17. Seriously Single (2020)

    While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.

    Why it matches: Recommended by TMDB viewers · both comedy

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  18. 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
  19. Wanda Sykes: Not Normal (2019)

    Wanda Sykes tackles politics, reality TV, racism and the secret she'd take to the grave in this rollicking, no-holds-barred stand-up special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  20. 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

Like Confessions of a Womanizer and something else?

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

Frequently asked questions

What are the best movies like Confessions of a Womanizer?

The closest matches to Confessions of a Womanizer are The F**k-It List (2020), Spa Weekend (2026) and Held Up (1999). Below are 17 more, each with the reason it matches.

What should I watch after Confessions of a Womanizer?

Start with The F**k-It List (2020), the closest match to Confessions of a Womanizer.

What is the highest-rated movie like Confessions of a Womanizer?

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

What is the newest movie like Confessions of a Womanizer?

Spa Weekend (2026) is the most recent release on this list.

Are there English movies like Confessions of a Womanizer?

Yes: The F**k-It List (2020), Spa Weekend (2026) and Held Up (1999).

How are movies similar to Confessions of a Womanizer chosen?

First come films that Trakt’s viewers watch alongside Confessions of a Womanizer, 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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