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Movies like Sadness (1999)

The best movies like Sadness (1999) are As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), Howard (2018) and Come See Me in the Good Light (2025). If Sadness hooked you with its documentary, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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 this
  2. Howard (2018)

    Though legendary lyricist Howard Ashman died far too young, his impact on Broadway, movies, and the culture at large were incalculable. Told entirely through rare archival footage and interviews with Ashman’s family, friends, associates, and longtime partner Bill Lauch, Howard is an intimate tribute to a once-in-a-generation talent and a rousing celebration of musical storytelling itself.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  3. Come 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 this
  4. 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 this
  5. Being James Bond (2021)

    Daniel Craig candidly reflects on his 15 year adventure as James Bond. Including never-before-seen archival footage from Casino Royale to the upcoming 25th film No Time To Die, Craig shares his personal memories in conversation with 007 producers, Michael G Wilson and Barbara Broccoli.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  6. John Candy: I Like Me (2025)

    Those who knew iconic funnyman John Candy best share his story, in their own words, through never-before-seen archival footage, imagery, and interviews.

    Why it matches: Recommended by TMDB viewers · both documentary

    Absolute CinemaMovies like this
  7. Charlie: The Life and Art of Charles Chaplin (2003)

    Brilliant, long in-the-works story of the life and art of the world's greatest comedian and the cinema's first genius, Charlie Chaplin. Produced, written and directed by renowned film critic Richard Schickel.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  8. The 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 this
  9. 28 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 this
  10. Evil Influencer: The Jodi Hildebrandt Story (2025)

    Unravel the case of Utah therapist Jodi Hildebrandt, whose child abuse arrest with parenting YouTuber Ruby Franke exposed a twisted tale of manipulation.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  11. 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 this
  12. Casting By (2012)

    This essential new documentary pays tribute to the legacy of the late, legendary casting director Marion Dougherty and shines a light on one of the most overlooked and least understood crafts in filmmaking.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  13. Cameraperson (2016)

    As a visually radical memoir, CAMERAPERSON draws on the remarkable footage that filmmaker Kirsten Johnson has shot and reframes it in ways that illuminate moments and situations that have personally affected her. What emerges is an elegant meditation on the relationship between truth and the camera frame, as Johnson transforms scenes that have been presented on Festival screens as one kind of truth into another kind of story—one about personal journey, craft, and direct human connection.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  14. Gilbert (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 this
  15. For the Love of Spock (2016)

    The life of Mr. Spock, as well as that of Leonard Nimoy, the actor who played him for almost fifty years, written and directed by his son: Adam.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  16. Chris 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 this
  17. Scotty 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 this
  18. My 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 this
  19. Everybody’s Everything (2019)

    The story of artist Lil Peep from his birth in Long Island and meteoric rise as a genre blending pop star & style icon, to his death due to an accidental opioid overdose in Arizona at just 21 years of age.

    Why it matches: Recommended by TMDB viewers · both documentary

    Absolute CinemaMovies like this
  20. I 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 this
  21. The Life of Rayful Edmond (2005)

    The true king of cocaine. At his peak he sold 2,000 kilos a week, reaped gross profits of $70 million a month, and ran an operation with over 150 soldiers to support him. In his life champagne flowed like water, trips to Vegas, New York, and Los Angeles were the norm, and $150,000 shopping sprees were nothing. At the height of Washington, D.C.'s brutal crack epidemic in 1987, there was a 22 year old man responsible for distributing 90% of Columbian Cocaine onto the city's streets. This man is Rayful Edmond III. In the media's eyes he was guilty until proven innocent, but in the streets eyes he was a hero who made it to the top. This is his story-a story of; Power, Money, Murder, Betrayal and the rise and fall of the Edmond's Empire.

    Why it matches: Similar story and style · both documentary

  22. De reparto: retrato de un actor (2009)

    Why it matches: Similar story and style · both documentary

  23. Orson Welles y Goya (2008)

    Why it matches: Similar story and style · both documentary

  24. The Cinema According to Dalí (2010)

    Why it matches: Similar story and style · both documentary

  25. Arne Sucksdorff: Uma Vida Documentando a Vida (2004)

    Why it matches: Similar story and style · both documentary

  26. Un instante en la vida ajena (2003)

    Compilation of images of the amateur recordings of Madronita Andreu, Catalan intellectual of the nineteenth century, daughter of Dr. Andreu, famous for its pills and cough syrup.

    Why it matches: Similar story and style · both documentary

  27. Flannery (2019)

    Explore the life of Flannery O’Connor whose provocative fiction was unlike anything published before. Featuring never-before-seen archival footage, newly discovered journals, and interviews with Mary Karr, Tommy Lee Jones, Hilton Als, and more.

    Why it matches: Similar story and style · both documentary

  28. Wonder Boy (2019)

    At age 25, Olivier Rousteing was named the creative director of the French luxury fashion house, Balmain. At the time, Rousteing was a relatively unknown designer, but in the decade since, he’s proven his business prowess and artistic instinct by leading Balmain to new heights. Wonderboy gives the viewer the rare opportunity to experience the inner sanctum of the fashion world, as we stand shoulder-to-shoulder with this extraordinary individual while he works.

    Why it matches: Similar story and style · both documentary

    Popcorn FlickMovies like this
  29. The Mentors: Kings of Sleaze Rockumentary (2017)

    Documentary on the shock rock group "The Mentors".

    Why it matches: Similar story and style · both documentary

  30. Milan Kundera: From the Joke to Insignificance (2021)

    The brilliant Czech writer Milan Kundera has not given an interview in thirty years; nor does he appear in public. How did he become a legendary author? What is so unique about his books?

    Why it matches: Similar story and style · both documentary

Like Sadness and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Sadness?

The closest matches to Sadness are As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), Howard (2018) and Come See Me in the Good Light (2025). Below are 27 more, each with the reason it matches.

What should I watch after Sadness?

Start with As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), the closest match to Sadness.

What is the highest-rated movie like Sadness?

Everybody’s Everything (2019), rated 8.4/10 by 311 TMDB users.

What is the newest movie like Sadness?

Evil Influencer: The Jodi Hildebrandt Story (2025) is the most recent release on this list.

Are there English movies like Sadness?

Yes: As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000), Howard (2018) and Come See Me in the Good Light (2025).

How are movies similar to Sadness chosen?

First come films that Trakt’s viewers watch alongside Sadness, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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