10 Documentaries That Won the Oscar for Best Documentary in the 20th Century

March 15, 2025

 

If you think documentaries are just dry educational films or nature specials narrated by a monotone voice, think again. The 20th century gave us some of the most groundbreaking, politically charged, and emotionally powerful documentaries—so powerful that they took home the coveted Academy Award for Best Documentary Feature. These films didn’t just inform audiences; they changed how we see the world.

 

The Oscars have long recognized outstanding documentary filmmaking, honoring works that expose uncomfortable truths, celebrate human resilience, or revolutionize the medium. From war and activism to personal struggles and artistic revolutions, these docs left a lasting impact on cinema and culture alike. These are not simply documentaries—they’re invitations to see the world as it truly is, in all its raw beauty and contradiction

 

If you’re wondering where to watch some of the best award-winning documentaries, you’re in the right place. This list of Oscar-winning films from the 20th century is a must for any documentary lover. And if you’re into deep dives on history, social issues, or just jaw-dropping real-life stories, these movies will be your next binge-watch.

 

Before diving into our list, let’s take a moment to appreciate what makes documentaries such a compelling form of storytelling. Unlike fiction films, docs have the power to uncover hidden truths, bring real-life heroes and villains to the forefront, and shake audiences to their core. Some documentaries are so impactful that they don’t just win Oscars—they shape history.

 

Looking for the most compelling documentaries of 2024? Dive into "The Best Documentaries of 2024: Stories That Defined a Transformative Year", where we highlight the most thought-provoking, visually stunning, and powerful films that defined the year. From groundbreaking investigative pieces to deeply personal stories, these must-watch docs capture the essence of our times. 

 

Take The Times of Harvey Milk (1984), for example. This gripping documentary didn’t just tell the story of a trailblazing politician; it became a powerful symbol of LGBTQI+ activism, bringing visibility to a movement that mainstream media often ignored. Meanwhile, The Last Days (1998) offered a harrowing look at the Holocaust through the stories of Hungarian Jews who survived Auschwitz, ensuring that history’s darkest chapters are never forgotten. These films do more than just entertain; they challenge perceptions, change minds, and leave a legacy.

 

10 Oscar-Winning Documentaries You Need to Watch:

 

 

  • The Times of Harvey Milk (1984)

  • Common Threads: Stories from the Quilt (1989)

  • American Dream (1990)

  • In the Shadow of the Stars (1991)

  • Maya Lin: A Strong Clear Vision (1994)

  • Anne Frank Remembered (1995) 

  • When We Were Kings (1996)

  • The Last Days (1998)

  • One Day in September (1999)

 

The Times of Harvey Milk (1984)

Decades before Milk (2008) starring Sean Penn, there was The Times of Harvey Milk. This compelling documentary tells the real-life story of the first openly gay elected official in California, his assassination, and the impact of his activism. Winning an Oscar solidified its importance as a milestone in LGBTQ+ history.

 

Common Threads: Stories from the Quilt (1989)

One of the most powerful documentaries on the AIDS epidemic, Common Threads tells the story of the NAMES Project AIDS Memorial Quilt and the lives behind each square. Narrated by Dustin Hoffman, the film personalizes the tragedy of the epidemic and sheds light on the devastating impact it had on a generation.

 

American Dream (1990)

A gripping account of the 1985-86 Hormel Foods strike in Minnesota, where workers took a stand after drastic wage and benefit cuts. As tensions rose between the company, union leaders, and striking employees, the battle became a defining moment in American labor history—one that tested loyalty, resilience, and the true cost of standing up for workers' rights.

 

In the Shadow of the Stars (1991)

This gripping documentary offers a witty and heartfelt glimpse into the world of opera—not from the perspective of the stars, but from those who dream of becoming them. With humor and charm, the film follows the unsung heroes of the stage—chorus members, understudies, and aspiring soloists—as they navigate ambition, talent, and the relentless pursuit of the spotlight in one of the most competitive art forms.

 

Maya Lin: A Strong Clear Vision (1994)

This powerful doc is an exploration of the groundbreaking artist and architect behind some of America’s most poignant monuments. Best known for the Vietnam Veterans Memorial and the Civil Rights Memorial, Maya Lin redefined public space with her minimalist yet deeply emotional designs. Through intimate interviews and behind-the-scenes footage, this documentary delves into her creative process, the

 

Anne Frank Remembered (1995) 

This poignant documentary traces the story of the Frank family, offering an intimate portrait of Anne Frank beyond the pages of her famous diary. Through rare archival footage, personal accounts, and historical context, the film captures the vibrant, free-spirited girl behind one of history’s most powerful testimonies. As the world’s most well-known victim of the Holocaust, Anne’s story is not just one of loss but of resilience, hope, and the enduring power of her words.

 

When We Were Kings (1996)

This action-packed documentary captures the tension, strategy, and sheer spectacle of one of boxing’s most iconic fights, revealing how Ali, the underdog, defied expectations with his now-famous “rope-a-dope” technique. More than just a sports story, it’s a testament to resilience, showmanship, and the power of mind over muscle.

 

The Last Days (1998)

In late 1944, as their downfall loomed, the Nazis launched one of their most brutal final acts—the mass deportation and extermination of over 425,000 Hungarian Jews. This Oscar-winning documentary, executive produced by Steven Spielberg, follows the harrowing journeys of five Hungarian Jewish survivors who endured the horrors of Auschwitz. Through their firsthand accounts, the film paints a haunting portrait of resilience in the face of unimaginable cruelty, ensuring that one of history’s darkest chapters is never forgotten.

 

One Day in September (1999)

This thrilling documentary revisits the 1972 Munich Olympics massacre, where Palestinian terrorists took Israeli athletes hostage. Combining archival footage with dramatic reenactments, One Day in September plays like a real-life spy thriller, keeping viewers on edge until the very last moment.

 

Why These Docs Still Matter Today

 

Each of these documentaries won an Oscar not just for their artistry but for their ability to start conversations. Whether exposing government secrets, capturing social revolutions, or simply preserving cultural history, these films remain essential viewing for anyone who wants to understand the 20th century.

 

In today’s age of streaming, it’s easier than ever to watch online and discover these award-winning gems. Platforms like Guidedoc specialize in curating high-quality docs, making it simple to find both classics and new groundbreaking films in one place. If you’re a documentary enthusiast, don’t just rely on Netflix or YouTube—dive deeper into dedicated platforms where true documentary storytelling thrives.

 

The best documentaries don’t just win awards; they redefine how we see the world. From The Times of Harvey Milk’s powerful portrayal of LGBTQI+ activism to Hearts and Minds’s hard-hitting war critique, these films continue to be relevant decades after their release.

 

So, if you’re looking to watch online and immerse yourself in films that have not only made history but also documented it, these ten Oscar-winning documentaries from the 20th century are the perfect place to start. And remember, the power of a documentary film lies in its ability to make us think, feel, and, most importantly, remember.

 

Watch more great documentaries on Guidedoc

 

 


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