Movies like Free Flying (2020)
The best movies like Free Flying (2020) are As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), 28 Up (1985) and Trainwreck: The Real Project X (2025). If Free Flying hooked you with its documentary, these 20 similar films are what to watch next, and every pick says why it matches.
Free Flying
Quick picks
- NewestA Toxic Love Story (2026)Released 2026
As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)
A compilation of over 30 years of private home movie footage shot by Lithuanian-American avant-garde director Jonas Mekas, assembled by Mekas "purely by chance", without concern for chronological order.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this28 Up (1985)
Just two years away from turning 30, participants in Michael Apted's documentary series are facing serious questions of identity and purpose, wondering whether they've found their place in the world.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisTrainwreck: The Real Project X (2025)
A night of drunken chaos rocks a quiet Dutch town in this shocking documentary about a teen's birthday invite that accidentally went viral on Facebook.
Why it matches: Recommended by TMDB viewers · both documentary
SnoozefestMovies like thisAnna Nicole Smith: You Don't Know Me (2023)
From the heights of her modeling fame to her tragic death, this documentary reveals Anna Nicole Smith through the eyes of the people closest to her.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMy Mom Jayne (2025)
Through deeply personal interviews with her siblings and an examination of the photographs, letters, and belongings left behind, Mariska assembles a new portrait of her mother Jayne Mansfield, an extraordinary and complex woman.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like this21 Up (1977)
After another 7 year wait, director Michael Apted revisits the same group of British-born children from Seven Up! and 7 Plus Seven. The subjects are interviewed as to the changes that have occurred in their lives during the last seven years.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisHalloween: 25 Years of Terror (2006)
Follow the evolution of the 'Halloween' movies over the past twenty-five years. It examines why the films are so popular and revisits many of the original locations used in the films - seeing the effects on the local community. For the first time, cast, crew, critics and fans join together in the ultimate 'Halloween' retrospective.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisThe U.S. vs. John Lennon (2006)
A documentary on the life of John Lennon, with a focus on the time in his life when he transformed from a musician into an antiwar activist.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisThe Curious Birth of Benjamin Button (2009)
A documentary about the making of David Fincher's 2008 film THE CURIOUS CASE OF BENJAMIN BUTTON. Virtually every element in the evolution of the Fincher's film is documented here, from the project's attachment to numerous other directors during the 1990s, to its shoot in 2006 and 2007 in New Orleans, to its complex, CGI-intensive postproduction process.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisCome See Me in the Good Light (2025)
In an intimate and joyful story of love in the face of loss, celebrated poets Andrea Gibson and Megan Falley find strength—and unexpected hilarity—in what might be their final year together.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this35 Up (1991)
Director Michael Apted revisits the same group of British-born adults after a 7 year wait. The subjects are interviewed as to the changes that have occurred in their lives during the last seven years.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisElstree 1976 (2015)
A documentary about ten very different lives connected by having appeared onscreen wearing masks or helmets in Star Wars.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisBright Lights: Starring Carrie Fisher and Debbie Reynolds (2016)
An intimate portrait of Hollywood royalty featuring Debbie Reynolds, Todd Fisher, and Carrie Fisher.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisSeven Up! (1985)
A group of British children aged 7 from widely ranging backgrounds are interviewed about a range of subjects. The filmmakers plan to re-interview them at 7 year intervals to track how their lives and attitudes change as they age.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisEx Libris: The New York Public Library (2017)
A documentary about how a dominant cultural and demographic institution both sustains their traditional activities and adapts to the digital revolution.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like this"Sr." (2022)
A portrait of the life and career of Robert Downey Sr. (1936-2021), the visionary and fearless US filmmaker — father of actor Robert Downey Jr. — who in the sixties and seventies laid the foundations for countercultural comedy.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisA Toxic Love Story (2026)
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisDirected by John Ford (1971)
A documentary about the life and films of director John Ford.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this56 Up (2012)
When a cross-section of seven-year-olds were interviewed for 7 Up in 1964 it was immediately evident that their social backgrounds influenced their attitudes towards life. While the upper class children were confident and self-assured, those from middle and working class backgrounds were resigned to a challenging life of hard work. This premise was put to the test every seven years when the same group were interviewed about the progression of their lives. 49 years in the making, the changes that occurred to the original 14 make for fascinating television and are in many ways the stories of all our lives. From success and disappointment, marriage and childbirth, to poverty and illness, nearly every facet of life has been captured on film. Now, at the age of 56, the group are once more brought together and, with the benefit of hindsight, assess whether their lives have been ruled by circumstance or self-determination.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisDrew: The Man Behind the Poster (2013)
A documentary on legendary movie-poster artist Drew Struzan.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Free Flying?
The closest matches to Free Flying are As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), 28 Up (1985) and Trainwreck: The Real Project X (2025). Below are 17 more, each with the reason it matches.
What should I watch after Free Flying?
Start with As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), the closest match to Free Flying.
What is the newest movie like Free Flying?
A Toxic Love Story (2026) is the most recent release on this list.
How are movies similar to Free Flying chosen?
First come films that Trakt’s viewers watch alongside Free Flying, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.