Movies like Free Spirit (2019)
The best movies like Free Spirit (2019) are How to Be Single (2016), June and John (2025) and Wonderstruck (2017). If Free Spirit hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedCarlito's Way (1993)7.8/10 from 3,651 votes
- NewestOne Night Only (2026)Released 2026
How to Be Single (2016)
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisJune and John (2025)
John leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his bumptious life.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWonderstruck (2017)
The story of a young boy in the Midwest is told simultaneously with a tale about a young girl in New York from fifty years ago as they both seek the same mysterious connection.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Age of Innocence (1993)
In 19th century New York high society, a young lawyer falls in love with a woman separated from her husband, while he is engaged to the woman's cousin.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisWhatever Works (2009)
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are quickly drawn into wildly unexpected romantic entanglements. Everyone discovers that finding love is just a combination of lucky chance and appreciating the value of "whatever works."
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThe True Adventures of Wolfboy (2019)
Follows a young boy who runs away from home in the search of his estranged mother.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisTigertail (2020)
A man reflects on the lost love of his youth and his long-ago journey from Taiwan to America as he begins to reconnect with his estranged daughter.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisG (2002)
A young Hip Hop star named Summer G falls for a middle to upper class sister while in college. After she rejects him for a fellow social climber, Summer G spends ten years building a Hip Hop empire, then moves to the Hamptons where he finds the object of his affections.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLondon (2005)
London is a drug laden adventure that centers on a party in a New York loft where a young man is trying to win back his ex-girlfriend.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisOne Night Only (2026)
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisStill Breathing (1997)
Two lost souls: she a con-artist in L.A.; he a puppeteer in San Antonio have the same dream linking each with the other. He travels to L.A. to find this woman he has become obsessed with. She resists, afraid of his kooky ideas until she travels with him to San Antonio and meets his wise grandmother. Story of two disparate people linked by "fate" gets increasingly interesting as it rolls along.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Map That Leads to You (2025)
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life choices test their bond, her path changes forever.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGreat Expectations (2012)
Orphan Pip discovers through lawyer Mr. Jaggers that a mysterious benefactor wishes to ensure that he becomes a gentleman. Reunited with his childhood patron, Miss Havisham, and his first love, the beautiful but emotionally cold Estella, he discovers that the elderly spinster has gone mad from having been left at the altar as a young woman, and has made her charge into a warped, unfeeling heartbreaker.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisCarlito's Way (1993)
Free after years in prison, Carlito Brigante intends to give up his criminal ways, but it's not long before the ex-con is sucked back into the New York City underworld.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies 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 thisA Night at the Roxbury (1998)
Despite being well into adulthood, brothers Doug and Steve Butabi still live at home and work in the flower shop owned by their dad. They exist only to hit on women at discos, though they're routinely unsuccessful until a chance run-in with Richard Grieco gets them inside the swank Roxbury club. Mistaken for high rollers, they meet their dream women, Vivica and Cambi, and resolve to open a club of their own.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Purple Rose of Cairo (1985)
Cecilia is a waitress in New Jersey, living a dreary life during the Great Depression. Her only escape from her mundane reality is the movie theatre. After losing her job, Cecilia goes to see 'The Purple Rose of Cairo' in hopes of raising her spirits, where she watches dashing archaeologist Tom Baxter time and again.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisTwo Lovers (2008)
A depressed man moves back in with his parents following a recent heartbreak and finds himself with two women.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe World of Henry Orient (1964)
A mischievous, adventuresome fourteen-year-old girl and her best friend begin following an eccentric concert pianist around New York City after she develops a crush on him.
Why it matches: Recommended by TMDB viewers
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Frequently asked questions
What are the best movies like Free Spirit?
The closest matches to Free Spirit are How to Be Single (2016), June and John (2025) and Wonderstruck (2017). Below are 17 more, each with the reason it matches.
What should I watch after Free Spirit?
Start with How to Be Single (2016), the closest match to Free Spirit.
What is the highest-rated movie like Free Spirit?
Carlito's Way (1993), rated 7.8/10 by 3,651 TMDB users.
What is the newest movie like Free Spirit?
One Night Only (2026) is the most recent release on this list.
Are there English movies like Free Spirit?
Yes: How to Be Single (2016), June and John (2025) and Wonderstruck (2017).
How are movies similar to Free Spirit chosen?
First come films that Trakt’s viewers watch alongside Free Spirit, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.