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Movies Like The Appointments of Dennis Jennings

If you liked The Appointments of Dennis Jennings (1988), a comedy movie directed by Dean Parisot, 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. 1Ricky 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.

  2. 2Ricky Gervais: Humanity

    Ricky Gervais: Humanity (2018)

    ★ 7.6/10Also comedy

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

  3. 3Spa Weekend

    Spa Weekend (2026)

    ★ 6.5/10Also comedy

    Four lifelong friends escape to a luxury spa retreat to reconnect, unwind and rediscover themselves, but their weekend of relaxation soon turns into a series of wild adventures and bad decisions.

  4. 4Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer

    Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)

    ★ 6.8/10Also comedy

    A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.

  5. 5How High

    How High (2001)

    ★ 6.4/10Also comedy

    Jamal and Silas, two ordinary guys who smoke something magical, pass their college entrance exams with flying colors and end up at Harvard. Ivy League ways are strange but Silas and Jamal take it in a stride -- until…

  6. 6The 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.

  7. 7Banana Split

    Banana Split (2018)

    ★ 6.6/10Also comedy

    After a messy breakup with her high school boyfriend, April strikes up an unexpected platonic friendship with his new girlfriend, Clara.

  8. 8Driver'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.

  9. 9John 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.

  10. 10Die, Mommie, Die!

    Die, Mommie, Die! (2003)

    ★ 6.6/10Also comedy

    Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her…

  11. 11One Night at McCool's

    One Night at McCool's (2001)

    ★ 5.9/10Also comedy

    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…

  12. 12Eenie Meanie

    Eenie Meanie (2025)

    ★ 6.3/10Also comedy

    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.

  13. 13Taylor Tomlinson: Look at You

    Taylor Tomlinson: Look at You (2022)

    ★ 7.2/10Also comedy

    Breakups. Therapy. Bangs. Taylor's gone through some stuff since her quarter-life crisis, and she spins her mental health journey into insightful comedy.

  14. 14Jackass Presents: Bad Grandpa

    Jackass Presents: Bad Grandpa (2013)

    ★ 6.2/10Also comedy

    86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.

  15. 15Hard to Die

    Hard to Die (1990)

    ★ 6/10Also comedy

    While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…

  16. 16Living in Oblivion

    Living in Oblivion (1995)

    ★ 7.2/10Also comedy

    Low-budget independent filmmaker Nick Reve tries to keep everything together as his production is plagued with an insecure actress, a megalomaniac star, a pretentious beret-wearing director of photography, and lousy…

  17. 17Joy Ride

    Joy Ride (2023)

    ★ 6.5/10Also comedy

    When Audrey's business trip to Asia goes sideways, she enlists the aid of Lolo, her irreverent, childhood best friend who also happens to be a hot mess; Kat, her college friend turned Chinese soap star; and Deadeye…

  18. 18The Dream Team

    The Dream Team (1989)

    ★ 6.1/10Also comedy

    Four mental patients on a field trip in New York City must save their caring chaperone, who ends up being taken to a hospital in a coma after accidentally witnessing a murder, before the killers can find him and finish…

  19. 19The Last American Virgin

    The Last American Virgin (1982)

    ★ 6.6/10Also comedy

    The friendship of a group of young friends struggling with teen sex, drugs, and work is jeopardized by a romantic interest which may turn pals into bitter rivals.

  20. 20Bill 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.

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