Movies like Summer Vacation 1999 (1988)
The best movies like Summer Vacation 1999 (1988) are Helter Skelter (2012), 20th Century Boys 3: Redemption (2009) and 20th Century Boys: Beginning of the End (2008). If Summer Vacation 1999 hooked you with its drama and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedGiven (2020)8.2/10 from 428 votes
- NewestHeartstopper Forever (2026)Released 2026
- In JapaneseHelter Skelter (2012)Also in Japanese
Helter Skelter (2012)
Top model Lilico, having recently undergone multiple cosmetic surgeries, begins to experience troubling side effects. As she desperately tries to retain her perfect image, Lilico descends into a world of nightmares and makes those around her miserable.
Why it matches: Fans watch both · both drama
Popcorn FlickMovies like this20th Century Boys 3: Redemption (2009)
The final showdown, and the final reveal. Who is Friend? How can he be stopped?
Why it matches: Fans watch both · both mystery
Popcorn FlickMovies like this20th Century Boys: Beginning of the End (2008)
In 1969, Kenji, an elementary school kid and his friends built a secret base during their summer holidays. They fantasized that they had to fight villains who were out to conquer the world and wrote them in the Book of Prophecies. Years later in 1997, Kenji becomes a convenience store manager and leads a regular life after giving up his dreams to become a rock star. His boring life is suddenly turned upside down when his old classmate dies mysteriously and an entire family in the neighbourhood disappears. At the same time, a religious cult and its mysterious leader, Friend emerges and a strange chain of events duplicating exactly the events described in the Book of Prophecies follow. Is this the beginning of the end of the world? Who is Friend?
Why it matches: Fans watch both · both mystery
Popcorn FlickMovies like thisMushi-Shi: The Movie (2007)
Mushi are beings in touch with the essence of life, far more basic and pure than normal living things. Most humans are incapable of perceiving Mushi and are oblivious to their existence, but there are a few who possess the ability to see and interact with Mushi. One such person is Ginko who travels from place to place to research Mushi and aid people suffering from problems caused by them.
Why it matches: Fans watch both · both fantasy
Popcorn FlickMovies like this20th Century Boys 2: The Last Hope (2009)
Set 15 years after "Twentieth Century Boys," Kanna (Airi Taira) reunites with several main characters from the first film in an attempt to stop Friend's increasing influence over the world and continued plans to eliminate humanity, as detailed in the New Book of Prophecy.
Why it matches: Fans watch both · both mystery
Popcorn FlickMovies like thisWinter's Tale (2014)
A burglar falls for an heiress as she dies in his arms. When he learns that he has the gift of reincarnation, he sets out to save her.
Why it matches: Recommended by TMDB viewers · both drama & fantasy
Popcorn FlickMovies like thisBig Bang Love, Juvenile A (2006)
An unknown future. A boy confesses to the murder of another in an all-boy juvenile detention facility. More an exercise in style than storytelling, the story follows two detectives trying to uncover the case. Homosexual tension and explosive violence drives the story which delivers some weird and fascinating visuals.
Why it matches: Recommended by TMDB viewers · both fantasy & mystery
Popcorn FlickMovies like thisPeter Ibbetson (1935)
When his mother dies, young Peter Ibbetson leaves Paris and his best friend, Mary, behind to live with a severe uncle in England. Years later, Peter is an architect with little time for women, until he begins a project with the Duke and Duchess of Towers. When Peter and the duchess become great friends, she reveals that she is Mary — but the duke soon suspects his wife of infidelity and challenges Peter to a duel, threatening the pair's second chance.
Why it matches: Recommended by TMDB viewers · both drama & fantasy
Worth the HypeMovies like thisPossession (2002)
Maud Bailey, a brilliant English academic, is researching the life and work of poet Christabel La Motte. Roland Michell is an American scholar in London to study Randolph Henry Ash, now best-known for a collection of poems dedicated to his wife. When Maud and Roland discover a cache of love letters that appear to be from Ash to La Motte, they follow a trail of clues across England, echoing the journey of the couple over a century earlier.
Why it matches: Recommended by TMDB viewers · both drama & mystery
Popcorn FlickMovies like thisJourney to the Shore (2015)
Mizuki's husband Yusuke has been missing for three years. He suddenly comes back home as a ghost and asks Mizuki to go on a trip with him. Their trip consists of visiting the people that helped Yusuke on his previous travel.
Why it matches: Recommended by TMDB viewers · both drama & fantasy
Popcorn FlickMovies like thisHeartstopper Forever (2026)
It's a new school year for the Truham-Higgs gang. As Nick and Charlie's relationship deepens, their thoughts turn to life after the last bell rings.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisAristotle and Dante Discover the Secrets of the Universe (2023)
Two teenage Mexican-American loners in 1987 El Paso explore a new, unusual friendship and the difficult road to self-discovery.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisYes, No, or Maybe? (2020)
A polished newscaster hides behind a mask when he meets a gentle artist—but the lie complicates everything when feelings start to grow.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisMarked Men: Rule + Shaw (2025)
Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — even if she’s the only one who can see the person he truly is. She lives by other people’s rules; he makes his own. But a short skirt, too many birthday cocktails, and spilled secrets lead to a night neither can forget. Now, Shaw and Rule must figure out how a girl like her and a guy like him are supposed to be together without destroying their love…or each other.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisEndless Love (2014)
A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisMy Policeman (2022)
In the late 1990s, the arrival of elderly invalid Patrick into Marion and Tom’s home triggers the exploration of seismic events from 40 years previous: the passionate relationship between Tom and Patrick at a time when homosexuality was illegal.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisGiven (2020)
Haruki secretly had feelings for Akihiko for years, but Akihiko was still in a relationship with his roommate, the violinist Ugetsu Murata. Haruki, Akihiko, and Ugetsu's love clashes and starts to move forward.
Why it matches: Recommended by TMDB viewers · both drama & romance
Absolute CinemaMovies like thisFire with Fire (1986)
A tough, street-smart kid serving a sentence in a state youth reformatory meets a beautiful, innocent girl studying at a nearby convent. When forbidden love blossoms between them, they must fight the prison authorities, their parents and the law.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisGo, Go Second Time Virgin (1969)
Go, Go, Second Time Virgin is the story of two damned and abused teenagers who meet and fall in mutant love on a Tokyo rooftop. Their only hope is to cement their love with an escape into oblivion.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisBlue Story (2019)
Blue Story is a tragic tale of a friendship between Timmy and Marco, two young boys from opposing postcodes. Timmy, a shy, smart, naive and timid young boy from Deptford, goes to school in Peckham where he strikes up a friendship with Marco, a charismatic, streetwise kid from the local area. Although from warring postcodes, the two quickly form a firm friendship until it is tested and they wind up on rival sides of a street war. Blue Story depicts elements of Rapman's own personal experiences and aspects of his childhood.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisSky of Love (2007)
Mika is a fresh high school student who starts texting a mysterious boy. She is shocked when he reveals who he is - Hiro, a delinquent attending her school. What she doesn't know is that Hiro isn't as bad as he seems.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisAfter (2019)
Tessa Young is a dedicated student, dutiful daughter and loyal girlfriend to her high school sweetheart. Entering her first semester of college, Tessa's guarded world opens up when she meets Hardin Scott, a mysterious and brooding rebel who makes her question all she thought she knew about herself -- and what she wants out of life.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisTuff Turf (1985)
The new guy in a Los Angeles high school, Morgan, does some singing and fights hotshot Nick over disco dancer Frankie.
Why it matches: Recommended by TMDB viewers · both drama & romance
SnoozefestMovies like thisThe Object of My Affection (1998)
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
Why it matches: Recommended by TMDB viewers · both drama & romance
SnoozefestMovies like thisDeparture (2016)
An English mother and her teenage son spend a week preparing the sale of their remote holiday house in the South of France. Fifteen-year-old Elliot struggles with his dawning sexuality and an increasing alienation from his mother, Beatrice. She in turn is confronted by the realisation that her marriage to his father, Philip, has grown loveless and the life she knows is coming to an end. When an enigmatic local teenager, Clément, quietly enters their lives, both mother and son are compelled to confront their desires and, finally, each other.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisAmerican 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 & mystery
Popcorn FlickMovies like thisKirepapa. (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 & drama
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 drama & romance
Little Gay Boy (2013)
A young gay boy, from his birth to his teenage years, in which he experiments his sexuality and his own boundaries, to the day he finally meets his father. In three acts: Act I — L'Annonciation or The Conception of a Little Gay Boy (2011); Act II — Little Gay Boy, ChrisT is Dead (2012); and Act III — Holy Thursday (The Last Supper) (2013).
Why it matches: Similar story and style · both drama & fantasy
Maria Watches Over Us (2010)
Yumi Fukuzawa is an ordinary first year student at Lillian Girls' Academy. By chance Yumi meets second year student Sachiko Ogasawara, who is a candidate to become a Red Rose. Sachiko later offers her rosary to Yumi Fukuzawa which signifies she will become an older sister to Yumi. Meanwhile, Yumi, who already looks up to popular Sachiko, is perplexed why she is picked. A festival named "Cinderella" then approaches, which is run by the Yamayuri Council. Conflicts between the older and younger sisters soon begins ...
Why it matches: Similar story and style · both drama & romance
Like Summer Vacation 1999 and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Summer Vacation 1999?
The closest matches to Summer Vacation 1999 are Helter Skelter (2012), 20th Century Boys 3: Redemption (2009) and 20th Century Boys: Beginning of the End (2008). Below are 27 more, each with the reason it matches.
What should I watch after Summer Vacation 1999?
People who watched Summer Vacation 1999 most often go on to Helter Skelter (2012), 20th Century Boys 3: Redemption (2009) and 20th Century Boys: Beginning of the End (2008).
What is the highest-rated movie like Summer Vacation 1999?
Given (2020), rated 8.2/10 by 428 TMDB users.
What is the newest movie like Summer Vacation 1999?
Heartstopper Forever (2026) is the most recent release on this list.
Are there Japanese movies like Summer Vacation 1999?
Yes: Helter Skelter (2012), 20th Century Boys 3: Redemption (2009) and 20th Century Boys: Beginning of the End (2008).
How are movies similar to Summer Vacation 1999 chosen?
First come films that Trakt’s viewers watch alongside Summer Vacation 1999, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.