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Movies Like The Philosophy of Dress

If you liked The Philosophy of Dress, a comedy movie directed by Cyrus Duff, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1Much Ado About Nothing

    Much Ado About Nothing (2013)

    ★ 6.8/10Also comedy

    A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

  2. 2Driver's Ed

    Driver's Ed (2026)

    ★ 6.9/10Also comedy

    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.

  3. 3Dave Chappelle: The Closer

    Dave Chappelle: The Closer (2021)

    ★ 7.2/10Also comedy

    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.

  4. 4Bill Burr: Drop Dead Years

    Bill Burr: Drop Dead Years (2025)

    ★ 7.2/10Also comedy

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

  5. 5Adam Sandler: Love You

    Adam Sandler: Love You (2024)

    ★ 6.3/10Also comedy

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

  6. 6Louis C.K.: Ridiculous

    Louis C.K.: Ridiculous (2026)

    ★ 6.1/10Also comedy

    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.

  7. 7Ricky Gervais: Mortality

    Ricky Gervais: Mortality (2025)

    ★ 7/10Also comedy

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

  8. 8LEGO Marvel Avengers: Mission Demolition

    LEGO Marvel Avengers: Mission Demolition (2024)

    ★ 6.5/10Also comedy

    A young, aspiring hero and superhero fan inadvertently unleashes a powerful new villain looking to rid the world of the Avengers.

  9. 9Taking Care of Business

    Taking Care of Business (1990)

    ★ 6.3/10Also comedy

    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.

  10. 10The Wedding Year

    The Wedding Year (2019)

    ★ 5.9/10Also comedy

    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.

  11. 11Nikki Glaser: Someday You'll Die

    Nikki Glaser: Someday You'll Die (2024)

    ★ 6.7/10Also comedy

    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.

  12. 12Class Rank

    Class Rank (2017)

    ★ 6.9/10Also comedy

    Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.

  13. 13Me Time

    Me Time (2022)

    ★ 5.8/10Also comedy

    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.

  14. 14Seriously Single

    Seriously Single (2020)

    ★ 6.8/10Also comedy

    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.

  15. 15Jerry Seinfeld: 23 Hours to Kill

    Jerry Seinfeld: 23 Hours to Kill (2020)

    ★ 6.2/10Also comedy

    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.

  16. 16Ricky Gervais: Armageddon

    Ricky Gervais: Armageddon (2023)

    ★ 7.1/10Also comedy

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

  17. 17Fun with Dick and Jane

    Fun with Dick and Jane (1977)

    ★ 6.6/10Also comedy

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

  18. 18John Mulaney: Kid Gorgeous at Radio City

    John Mulaney: Kid Gorgeous at Radio City (2018)

    ★ 7.9/10Also comedy

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

  19. 19I Love My Dad

    I Love My Dad (2022)

    ★ 5.9/10Also comedy

    A hopelessly estranged father catfishes his son in an attempt to reconnect.

  20. 20Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry

    Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)

    ★ 7/10Also comedy

    Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.

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