Movies like A 25 Year Old Gay Man Loses His Virginity to a Woman (1990)
The best movies like A 25 Year Old Gay Man Loses His Virginity to a Woman (1990) are Anna Nicole Smith: You Don't Know Me (2023), Strip Down, Rise Up (2021) and Ex Libris: The New York Public Library (2017). If A 25 Year Old Gay Man Loses His Virginity to a Woman hooked you with its documentary, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedI Am Heath Ledger (2017)7.4/10 from 233 votes
- NewestCome See Me in the Good Light (2025)Released 2025
Anna 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 thisStrip Down, Rise Up (2021)
The feature documentary follows women of all walks of life, all ages and ethnic backgrounds, as they shed trauma, body image shame, sexual abuse and other issues locked in their bodies, and embark on a journey to reclaim themselves. The film also gives a rare window into the world of Pole artistry and expression.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies 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 thisThe Curse of the Dragon (1993)
A 1993 documentary film about Bruce Lee. The film includes interviews from some of his fellow students and opponents who worked alongside him in his movies.
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 thisAmerican Boy: A Profile of Steven Prince (1978)
Martin Scorsese spends an evening with larger-than-life raconteur Steven Prince—a former drug addict, road manager for Neil Diamond, and actor—as he recounts stories from his colorful life.
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 thisI Am Heath Ledger (2017)
The life and career of an actor, artist, and icon. His own journey through his own camera.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisI Am Ali (2014)
Unprecedented access to Muhammad Ali's personal archive of "audio journals" as well as interviews and testimonials from his inner circle of family and friends are used to tell the legend's life story.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisAs 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 thisGirl Model (2011)
A documentary on the modeling industry's 'supply chain' between Siberia, Japan, and the U.S., told through the experiences of the scouts, agencies, and a 13-year-old model.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisSeduced and Abandoned (2013)
SEDUCED AND ABANDONED combines acting legend Alec Baldwin with director James Toback as they lead us on a troublesome and often hilarious journey of raising financing for their next feature film. Moving from director to financier to star actor, the two players provide us with a unique look behind the curtain at the world's biggest and most glamourous film festival, shining a light on the bitter-sweet relationship filmmakers have with Cannes and the film business. Featuring insights from directors Martin Scorsese, 'Bernando Bertolucci' and Roman Polanski; actors Ryan Gosling and Jessica Chastain and a host of film distribution luminaries.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisOrgasm Inc: The Story of OneTaste (2022)
A sexual wellness company gains fame and followers, then members come forward with shocking allegations.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisA Decade Under the Influence (2003)
A documentary examining the decade of the 1970s as a turning point in American cinema. Some of today's best filmmakers interview the influential directors of that time.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like thisMemories of a Murderer: The Nilsen Tapes (2021)
Serial killer Dennis Nilsen narrates his life and horrific crimes via a series of chilling audiotapes recorded from his jail cell.
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 thisX-Rated 2: The Greatest Adult Stars of All Time (2016)
Documentary sequel that offers a close-up look into the personal lives of the legendary porn stars who've survived the test of time and influenced popular culture. Blends rare interviews with erotic clips and additional appearances by Whoopi Goldberg, Steven Soderbergh and a host of adult stars, directors and trendsetters.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisAbove Majestic (2018)
A look at the origins, history and conspiracies behind the "Majestic 12", a clandestine group of military and corporate figureheads charged with reverse-engineering extraterrestrial technology.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisChris Brown: Welcome to My Life (2017)
This compelling Documentary moves beyond the spotlight and past the attention-grabbing headlines to give pop superstar Chris Brown a chance to tell his own story. New interviews with the international phenomenon reveal long-awaited answers about his passion for making music, his tumultuous and much publicized relationships, and the pitfalls of coming of age in the public eye. Also included is new concert footage, behind-the-scenes access, and special interviews from Usher, Jennifer Lopez, DJ Khaled, Mike Tyson, Jamie Foxx and others.
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 thisSpace in the Brain (1969)
Image analysis in slow motion. Distortion and reversed reality perspective.
Why it matches: Similar story and style · both documentary
Fantastic Vision (1957)
Footage filmed in Spain, subjected a new visual effects process. Deslaw devoted himself to the discovery of a new machine that enabled film to be developed while using a new method called solarisation.
Why it matches: Similar story and style · both documentary
Thot-Fal'N (1978)
This film describes a psychological state "kin to moonstruck, its images emblems (not quite symbols) of suspension-of-self within consciousness and then that feeling of falling away from conscious thought. The film can only be said to describe or be emblematic of this state because I cannot imagine symbolizing or otherwise representing an equivalent of thoughtlessness itself. Thus the actors in the film, Jane Brakhage, Tom and Gloria Bartek, Williams Burroughs, Allen Ginsberg, Peter Olovsky and Phillip Whalen are figments of this 'Thought-Fallen Process', as are their images in the film to find themselves being photographed."
Why it matches: Similar story and style · both documentary
Adios amigo mío, sin gestos, sin palabras (2015)
The title comes from Sergei Yesenin's last poem before comiting suicide. Using Virginia Woolf's last letters as a base, this film is meditation on the power of the word and its undertsanding and the the last moments before saying "goodbye".
Why it matches: Similar story and style · both documentary
A Messenger from the Shadows (Notes on Film 06 A/Monologue 01) (2013)
Thanks to his myriad film roles, Lon Chaney is known as “the man of a thousand faces,” and you could say that the early horror era never beheld a figure more intriguing. Yet because of his numerous transformations, his face never became as iconic as that of, say, Boris Karloff. Accompanied by a soundtrack from Bernhard Lang, this “re-imagination of shots” taken from Chaney´s forty-six surviving films offers a beguiling excursion into the history of film. The director reveals surprising associations, while highlighting the enduring magic of works which are now more or less forgotten.
Why it matches: Similar story and style · both documentary
The End of Time (2017)
An experimental film about that one hypnotic moment on a regular, unassuming Tuesday when one realizes that time has stopped and the universe has been sucked into a single smile.
Why it matches: Similar story and style · both documentary
The Earth (1961)
Short experimental 16mm film.
Why it matches: Similar story and style · both documentary
Roundabout (1962)
Short experimental 16mm film.
Why it matches: Similar story and style · both documentary
Men Boxing (1891)
Experimental film fragment made with the Edison-Dickson-Heise experimental horizontal-feed kinetograph camera and viewer, using 3/4-inch wide film.
Why it matches: Similar story and style · both documentary
SnoozefestMovies like thisStunned, I Remain Alert (2020)
Journalist Dermi Azevedo has never stopped fighting for human rights and now, three decades after the end of the military dictatorship in Brazil, he's witnessing the return of those same practices.
Why it matches: Similar story and style · both documentary
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Frequently asked questions
What are the best movies like A 25 Year Old Gay Man Loses His Virginity to a Woman?
The closest matches to A 25 Year Old Gay Man Loses His Virginity to a Woman are Anna Nicole Smith: You Don't Know Me (2023), Strip Down, Rise Up (2021) and Ex Libris: The New York Public Library (2017). Below are 27 more, each with the reason it matches.
What should I watch after A 25 Year Old Gay Man Loses His Virginity to a Woman?
Start with Anna Nicole Smith: You Don't Know Me (2023), the closest match to A 25 Year Old Gay Man Loses His Virginity to a Woman.
What is the highest-rated movie like A 25 Year Old Gay Man Loses His Virginity to a Woman?
I Am Heath Ledger (2017), rated 7.4/10 by 233 TMDB users.
What is the newest movie like A 25 Year Old Gay Man Loses His Virginity to a Woman?
Come See Me in the Good Light (2025) is the most recent release on this list.
Are there English movies like A 25 Year Old Gay Man Loses His Virginity to a Woman?
Yes: Anna Nicole Smith: You Don't Know Me (2023), Strip Down, Rise Up (2021) and Ex Libris: The New York Public Library (2017).
How are movies similar to A 25 Year Old Gay Man Loses His Virginity to a Woman chosen?
First come films that Trakt’s viewers watch alongside A 25 Year Old Gay Man Loses His Virginity to a Woman, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.