Movies like Dear Roy, Love Gillian (1992)
The best movies like Dear Roy, Love Gillian (1992) are The United States of Leland (2003), In the Good Old Summertime (1949) and Fire with Fire (1986). If Dear Roy, Love Gillian hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedMary and Max (2009)7.9/10 from 2,379 votes
- NewestThe Other Zoey (2023)Released 2023
The United States of Leland (2003)
A withdrawn young man, Leland Fitzgerald is imprisoned for the murder of a mentally disabled boy, who also happened to be the brother of his girlfriend, Becky. As the community struggles to deal with the killing, Pearl Madison, a teacher at the prison, decides to write about Leland's case. Meanwhile, others affected by the murder, including Becky and her sister, Julie, must contend with their own problems.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIn the Good Old Summertime (1949)
Two co-workers in a music shop dislike one another during business hours but unwittingly carry on an anonymous romance through the mail.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies 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
Popcorn FlickMovies like thisPaper Towns (2015)
Quentin Jacobsen has spent a lifetime loving the magnificently adventurous Margo Roth Spiegelman from afar. So when she cracks open a window and climbs back into his life dressed like a ninja and summoning him for an ingenious campaign of revenge, he follows. After their all-nighter ends and a new day breaks, Quentin arrives at school to discover that Margo, always an enigma, has now become a mystery. But Quentin soon learns that there are clues, and they're for him. Urged down a disconnected path, the closer Quentin gets, the less he sees of the girl he thought he knew.
Why it matches: Recommended by TMDB viewers
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
Popcorn FlickMovies like thisThe Mustang (2019)
While participating in a rehabilitation program training wild mustangs, a convict at first struggles to connect with the horses and his fellow inmates, but he learns to confront his violent past as he soothes an especially feisty horse.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisKeith (2008)
Natalie is high school royalty, but her queen bee status falls apart when she falls for the new guy at school. Although Keith ignores her at first, they soon become friends -- even though Natalie suspects that Keith has something to hide. As the free-spirited Keith shows Natalie how to embrace what life offers, they grow closer -- until a secret tests the bounds of their relationship
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies 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
Worth the HypeMovies like thisMary and Max (2009)
A tale of friendship between two unlikely pen pals: Mary, a lonely, eight-year-old girl living in the suburbs of Melbourne, and Max, a forty-four-year old, severely obese man living in New York.
Why it matches: Recommended by TMDB viewers
Absolute CinemaMovies like thisBanana Split (2018)
After a messy breakup with her high school boyfriend, April strikes up an unexpected platonic friendship with his new girlfriend, Clara.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisI Never Promised You a Rose Garden (1977)
A disturbed and institutionalized 16-year-old girl struggles between fantasy and reality.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisLove, Rosie (2014)
Since the moment they met at age 5, Rosie and Alex have been best friends, facing the highs and lows of growing up side by side. A fleeting shared moment, one missed opportunity, and the decisions that follow send their lives in completely different directions. As each navigates the complexities of life, love, and everything in between, they always find their way back to each other - but is it just friendship, or something more?
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisHeathers (1989)
A girl who halfheartedly tries to be part of the "in crowd" of her school meets a rebel who teaches her a more devious way to play social politics: by killing the popular kids.
Why it matches: Recommended by TMDB viewers
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
Worth the HypeMovies like thisMr. Right (2016)
A girl falls for the "perfect" guy, who happens to have a very fatal flaw: he's a hitman on the run from the crime cartels who employ him.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Unforgivable (2021)
A woman is released from prison after serving a sentence for a violent crime and re-enters a society that refuses to forgive her past.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisSecret Admirer (1985)
An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGoodbye, Mr. Chips (1969)
Academy Award-honoree Peter O'Toole stars in this musical classic about a prim English schoolmaster who learns to show his compassion through the help of an outgoing showgirl. O'Toole, who received his fourth Oscar-nomination for this performance, is joined by '60s pop star Petula Clark and fellow Oscar-nominee Michael Redgrave.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Other Zoey (2023)
Highly intelligent computer major Zoey Miller is uninterested in romantic love, but her life is turned upside down when Zack, the school's soccer star, gets amnesia and mistakes Zoey for his girlfriend.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Best of Me (2014)
A pair of former high school sweethearts reunite after many years when they return to visit their small hometown.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Dear Roy, Love Gillian?
The closest matches to Dear Roy, Love Gillian are The United States of Leland (2003), In the Good Old Summertime (1949) and Fire with Fire (1986). Below are 17 more, each with the reason it matches.
What should I watch after Dear Roy, Love Gillian?
Start with The United States of Leland (2003), the closest match to Dear Roy, Love Gillian.
What is the highest-rated movie like Dear Roy, Love Gillian?
Mary and Max (2009), rated 7.9/10 by 2,379 TMDB users.
What is the newest movie like Dear Roy, Love Gillian?
The Other Zoey (2023) is the most recent release on this list.
Are there English movies like Dear Roy, Love Gillian?
Yes: The United States of Leland (2003), In the Good Old Summertime (1949) and Fire with Fire (1986).
How are movies similar to Dear Roy, Love Gillian chosen?
First come films that Trakt’s viewers watch alongside Dear Roy, Love Gillian, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.