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Movies like My Summer Vacation (1996)

The best movies like My Summer Vacation (1996) are The Myth of the American Sleepover (2011), Benjamin (2019) and The Giant Mechanical Man (2012). If My Summer Vacation hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Myth of the American Sleepover (2011)

    Four young people navigate the suburban wonderland of metro-Detroit looking for love and adventure on the last weekend of summer.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  2. Benjamin (2019)

    Benjamin, a rising star filmmaker, is on the brink of premiering his difficult second film No Self at the London Film Festival when Billie, his hard drinking publicist, introduces him to a mesmeric French musician called Noah.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  3. The Giant Mechanical Man (2012)

    An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  4. Shag (1989)

    Summer of 1963. Carson is getting married to her boyfriend so her friends Melaina, Pudge and Luanne take her to Myrtle Beach for one last irresponsible weekend.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  5. Sidewalks of New York (2001)

    The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  6. Cosi (1996)

    Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  7. Camille (2008)

    A twisted honeymoon adventure about a young couple on their way to Niagara Falls.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  8. The Four Seasons (1981)

    Three middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  9. Happythankyoumoreplease (2011)

    Six New Yorkers navigate love, commitment, and adulthood. When struggling novelist Sam takes in an abandoned boy he meets on the subway, his life begins to intertwine with a talented singer who challenges his bachelor ways. Meanwhile, his best friend Annie battles alopecia while torn between two drastically different men, and a long-term couple faces a crossroads that could alter their future together.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  10. The Broken Hearts Club: A Romantic Comedy (2000)

    A close-knit group of gay friends share the emotional roller coster of life, relationships, the death of friends, new beginnings, jealousy, fatherhood and professional success. At various stages of life's disarray, these young men share humorous and tragic relationships and always have each other to rely on.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  11. Sex and the City 2 (2010)

    Carrie, Charlotte, and Miranda are all married now, but they're still up for a little fun in the sun. When Samantha gets the chance to visit one of the most extravagant vacation destinations on the planet and offers to bring them all along, they surmise that a women-only retreat may be the perfect excuse to eschew their responsibilities and remember what life was like before they decided to settle down.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  12. The Baltimorons (2025)

    A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  13. Chéri (2009)

    The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

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  14. Boy Meets Girl (2014)

    In Kentucky, a transgender woman and her best male friend lament the lack of eligible partners and step across old boundaries of love and romance.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  15. People We Meet on Vacation (2026)

    Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  16. My Fake Boyfriend (2022)

    A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  17. The Last Summer (2019)

    Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  18. Looking: The Movie (2016)

    Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

    Why it matches: Recommended by TMDB viewers · both drama & romance

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  19. Bros (2022)

    Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  20. The Thing About Harry (2020)

    Two high school enemies, uber-jock Harry and out-and-proud Sam, are forced to share a car ride to their Missouri hometown for a friend's engagement party on Valentine's Day. Things take a turn when Sam learns Harry has come out.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  21. Kirepapa. (2008)

    Chisato is a beautiful 35-year-old writer, who looks like 18, and the father of Riju, a cute 15-year-old boy. Chisato's hobby is to drive away all of Riju's friends because he thinks they want to corrupt his precious child, so he shows his good side to these boys while he poisons the cake he brings them with a smile; however, there is one guy, Shunsuke, who doesn't fall for the tricks. But is Shunsuke really aiming for Riju? Who is that mysterious writer Chisato loves so much? And why is Chisato convinced that Riju's friends want to take advantage of him?

    Why it matches: Similar story and style · both romance & comedy

  22. Love Bites (2025)

    Just out of their teens, young men Liam and Anatole were in the throes of an exciting relationship- until they had fight, and Anatole disappeared. Liam can’t accept breakup. And, since his boyfriend doesn’t reply to his calls and text messages, Liam decides to follow him to a Halloween organized by one of Anatole’s friends to try find him. The wild night that ensues will test boys’ true feelings for each other, as well as force them to confront some hard inner truths once and for all.

    Why it matches: Similar story and style · both comedy & drama

  23. Law of Desire (1987)

    Pablo, a successful film director, disappointed in his relationship with his young lover, Juan, concentrates in a new project, a monologue starring his transgender sister, Tina. Antonio, an uptight young man, falls possessively in love with the director and in his passion would stop at nothing to obtain the object of his desire.

    Why it matches: Similar story and style · both drama & romance

    Worth the HypeMovies like this
  24. The Adventures of Priscilla, Queen of the Desert (1994)

    Two drag performers and a transgender woman travel across the desert to perform their unique style of cabaret.

    Why it matches: Similar story and style · both drama & comedy

    Worth the HypeMovies like this
  25. Reflections in a Golden Eye (1967)

    Bizarre tale of sex, betrayal, and perversion at a military post.

    Why it matches: Similar story and style · both drama & romance

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  26. I Now Pronounce You Chuck & Larry (2007)

    Firefighters Chuck Ford and Larry Valentine are guy's guys, loyal to the core—which is why when widower Larry asks Chuck to pose as his lover so that he can get domestic partner benefits for his kids, his buddy agrees. However, things get dicey when a bureaucrat comes calling, and the boys are forced to present a picture of domestic bliss.

    Why it matches: Similar story and style · both comedy & romance

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  27. American Gigolo (1980)

    Julian makes a lucrative living as an escort to older women in the Los Angeles area. He begins a relationship with Michelle, a local politician's wife, without expecting any pay. One of his clients is murdered and Detective Sunday begins pumping him for details on his different clients, something he is reluctant to do considering the nature of his work. Julian begins to suspect he's being framed. Meanwhile Michelle begins to fall in love with him.

    Why it matches: Similar story and style · both drama

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  28. The Mousetrap (2016)

    Baptiste is a gay man who can't stop dreaming about a woman who works at a local pub. His desire for her makes him go on a journey that he could had never imagined.

    Why it matches: Similar story and style · both drama

  29. I Am Curious Gay (1970)

    On his 21st birthday, Davy wanders into a gay bar and meets the man of his dreams.

    Why it matches: Similar story and style · both drama

  30. Walk a Crooked Path (1969)

    Set in an exclusive boy's school, about a man who plans to kill off his wealthy teacher wife by encouraging her to drink and pushing her into suicide. To assist him he recruits a young student who will claim that he was sexually assaulted by her. (from: http://ftvdb.bfi.org.uk/sift/title/390627)

    Why it matches: Similar story and style · both drama

Like My Summer Vacation and something else?

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

Frequently asked questions

What are the best movies like My Summer Vacation?

The closest matches to My Summer Vacation are The Myth of the American Sleepover (2011), Benjamin (2019) and The Giant Mechanical Man (2012). Below are 27 more, each with the reason it matches.

What should I watch after My Summer Vacation?

Start with The Myth of the American Sleepover (2011), the closest match to My Summer Vacation.

What is the highest-rated movie like My Summer Vacation?

The Adventures of Priscilla, Queen of the Desert (1994), rated 7.3/10 by 979 TMDB users.

What is the newest movie like My Summer Vacation?

People We Meet on Vacation (2026) is the most recent release on this list.

Are there English movies like My Summer Vacation?

Yes: The Myth of the American Sleepover (2011), Benjamin (2019) and The Giant Mechanical Man (2012).

How are movies similar to My Summer Vacation chosen?

First come films that Trakt’s viewers watch alongside My Summer Vacation, 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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