Movies like Key West: The Hemingway's Island (2023)
The best movies like Key West: The Hemingway's Island (2023) are I Am Heath Ledger (2017), Struggle: The Life and Lost Art of Szukalski (2018) and Come See Me in the Good Light (2025). If Key West: The Hemingway's Island hooked you with its documentary, these 20 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
- In ItalianSergio Leone: The Italian Who Invented America (2022)Also in Italian
I 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 thisStruggle: The Life and Lost Art of Szukalski (2018)
Artists in LA discover the work of forgotten Polish sculptor Stanislav Szukalski, a mad genius whose true story unfolds chapter by astounding chapter.
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 thisThe Mole: Undercover in North Korea (2020)
A real-life undercover thriller about two ordinary men who embark on an outrageously dangerous ten-year mission to penetrate the world's most secretive and brutal dictatorship: North Korea.
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 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 thisGilbert (2017)
The life and career of one of comedy's most inimitable modern voices, Mr. Gilbert Gottfried.
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 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 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 thisScotty and the Secret History of Hollywood (2018)
A deliciously scandalous portrait of unsung Hollywood legend Scotty Bowers, whose bestselling memoir chronicled his decades spent as sexual procurer to the stars.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisRoman Polanski: A Film Memoir (2012)
An interview with film director Roman Polanski conducted during his period of house arrest, discussing his life and work.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisCameraman: The Life and Work of Jack Cardiff (2010)
In 2001 Jack Cardiff (1914-2009) became the first director of photography in the history of the Academy Awards to win an Honorary Oscar. But the first time he clasped the famous statuette in his hand was a half-century earlier when his Technicolor camerawork was awarded for Powell and Pressburger's Black Narcissus. Beyond John Huston's The African Queen and King Vidor's War and Peace, the films of the British-Hungarian creative duo (The Red Shoes and A Matter of Life and Death too) guaranteed immortality for the renowned cameraman whose career spanned seventy years.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMea Maxima Culpa: Silence in the House of God (2012)
Alex Gibney explores the charged issue of pedophilia in the Catholic Church, following a trail from the first known protest against clerical sexual abuse in the United States and all way to the Vatican.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisThe Assassination of Jesse James: Death of an Outlaw (2008)
Explores the true story of the notorious Jesse James, how the myth developed during his lifetime, and how the legends have persisted over 100 years after his death at the hands of his former friend, Robert Ford.
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 thisSergio Leone: The Italian Who Invented America (2022)
To mark the recent thirtieth anniversary of Sergio Leone’s death, this documentary sets out to pay tribute to one of the great legends of world cinema. The singular artistic vision of Sergio Leone has transcended national borders, creating the Spaghetti Western genre and transforming the international cinematic panorama forever with his innovative stylistic and narrative solutions, which have now become part of the language of the movies. The film, which is enriched with precious archive footage from the Cineteca di Bologna, including rare audio recordings and film clips shot behind the scenes, sees for the first time the direct participation of the Leone family and has interviews both with Leone’s longtime collaborators and with icons of Hollywood who have been profoundly influenced by his work.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisReMastered: The Two Killings of Sam Cooke (2019)
This investigation examines the mysterious shooting of soul icon Sam Cooke, whose death silenced one of the most vital voices in the civil rights movement.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMcQueen (2018)
Alexander McQueen's rags-to-riches story is a modern-day fairy tale, laced with the gothic. Mirroring the savage beauty, boldness and vivacity of his design, this documentary is an intimate revelation of McQueen's own world, both tortured and inspired, which celebrates a radical and mesmerizing genius of profound influence.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies 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 this
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Frequently asked questions
What are the best movies like Key West: The Hemingway's Island?
The closest matches to Key West: The Hemingway's Island are I Am Heath Ledger (2017), Struggle: The Life and Lost Art of Szukalski (2018) and Come See Me in the Good Light (2025). Below are 17 more, each with the reason it matches.
What should I watch after Key West: The Hemingway's Island?
Start with I Am Heath Ledger (2017), the closest match to Key West: The Hemingway's Island.
What is the highest-rated movie like Key West: The Hemingway's Island?
I Am Heath Ledger (2017), rated 7.4/10 by 233 TMDB users.
What is the newest movie like Key West: The Hemingway's Island?
Come See Me in the Good Light (2025) is the most recent release on this list.
Are there Italian movies like Key West: The Hemingway's Island?
Yes: Sergio Leone: The Italian Who Invented America (2022).
How are movies similar to Key West: The Hemingway's Island chosen?
First come films that Trakt’s viewers watch alongside Key West: The Hemingway's Island, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.