Jacob Osborn

24 Best Documentaries of All Time | Man of Many

His name is Rodriguez and he just might be the greatest folk artist you’ve never heard of…until now. Discover the true story of this mysterious Detroit-based musician, who failed to break out in the states but became a legend in South Africa.

1. Searching for Sugarman

Iconic singer Amy Winehouse took the planet by storm before succumbing to the pitfalls of addiction and success. Culled from behind-the-scenes footage, this gripping doc puts you in the passenger seat for her meteoric rise and dramatic fall. While utterly tragic, it’s also one of the best documentaries of all time.

2. AMY

Three identical twins are separated at birth and unaware of each other’s existence. One of the twins goes to college and gets mistaken for the other twin and eventually all three get in touch. It only gets weirder from there.

3. Three Identical Strangers

At the age of 18, Alex Lewis lost his memory after a motorcycle accident. With help from his twin brother, he pieces together the fragments of his missing past. As it turns out, his brother is leaving out a shocking secret.

4. Tell Me Who I Am

One of the best documentaries of all time tells a story of persistence, practice, and triumph. Set in 1974, it follows tightrope walker Philippe Petit as he prepares for (and executes) the ultimate challenge: an illegal high-wire routine between New York’s Twin Towers.

5. Man on Wire

The story of Kurt Cobain’s rise and fall is about as depressing as most of his songwriting output would suggest. Nevertheless, this revealing and uncompromising documentary is a must-watch for Nirvana fans. It features material and footage from Cobain’s own archives and paints a fairly bleak portrait of the iconic artist.

6. Kurt Cobain: Montage of Heck

Artist and activist James Baldwin was not your negro and he’s got the legacy to prove it.  This Oscar-nominated doc puts that legacy centre-stage as it tells the story of racial injustice by way of Baldwin’s unfinished novel, “Remember this House.” Actor Samuel L. Jackson narrates.

7. I Am Not Your Negro

Crime documentaries wouldn’t be what they are today if not for this 2003 film, about a seemingly normal upper-middle-class Jewish family. Lurking beyond the mundane facade is an unspeakable secret of disastrous proportions. The extensive use of home footage makes a creepy thing that much creepier.

8. Capturing the Friedmans

Calling all foodies! This is one of the best documentaries about not just the art of sushi, but dedication to craftsmanship in general. You will be both hungry and inspired by the time it’s over.

9. Jiro Dreams of Sushi

The Artinian family has both deaf members and non-deaf members alike. When five-year-old Heather is given the potential chance to hear, she must choose between two worlds.

10. Sound and Fury

At the height of the AIDS epidemic, cries for help were met with various forms of indifference and hostility at the highest of levels. This documentary chronicles the efforts of coalitions and activists, who fought back using every tool in their arsenal.

11. How to Survive a Plague

This sprawling masterpiece was part of ESPN’s 30-for-30 series, but don’t confuse it with your standard sports documentary. On the contrary, it brings you the “trial of the century” as you’ve never seen or understood it before. Not a single minute is wasted during the 7+ hour runtime.

12. O.J.: Made in America

Documentarian Barbara Kopple takes you deep into a 1973 coalminer’s strike, which lasted over a year and delivered no shortage of violent confrontations. What emerges is a striking portrait of blue-collar America and an Oscar-winning one at that.

13. Harlan County, USA

One of the best sports documentaries of all time follows two inner-city basketball players as they pursue their athletic dreams. Their respective journeys are chronicled as they unfold, meaning the filmmakers had no idea where each one was going. To say anything more is to ruin the experience so just watch it.

14. Hoop Dreams

Shining a light on America’s prison system, Ava DuVernay exposes racial injustice from both a historical and contemporary perspective. If you’re not mad, then you’re not paying attention.

15. 13th

Turning schadenfreude into a work of art, this documentary chronicles the disastrous Fyre music festival. Prepare to point and laugh.

16. Fyre

What begins as a sports documentary about athletic doping becomes a white-knuckle thriller with geopolitical dimensions. Don’t miss it.

17. Icarus

Former Indonesian death squad leaders reenact their previous deeds with a cinematic flourish and personal zest. This might be one of the best documentaries of all time, but it’s also one of the most disturbing. You’ve been warned.

18. The Act of Killing

Here’s a documentary so influential that it actually prompted SeaWorld to end its orca breeding program. You may never look at animal captivity the same way again.

19. Blackfish

Can filmmaker Michael Moore be overly sentimental or downright manipulative on occasion? Yes, he can. But he also makes some of the best documentaries of all time and this is one of them. In fact, some might say it kicked off the modern era.

20. Bowling for Columbine

The true David and Goliath battle, When We Were Kings tells the tale of former World Heavyweight Champion Mohammad Ali returning to the arena against a far younger and more favoured opponent. The documentary sheds a light on the preparation and pre-fight drama that foreshadowed the most famous boxing match of all time; Rumble in the Jungle.

21. When We Were Kings

Two hardcore “Donkey Kong” gamers square off for the title of supreme champion and the battle is as epic as it is unbelievable. You will be entertained!

22. King of Kong: A Fistful of Quarters

This insane documentary from Banksy is even more clever and satirical than you’d expect it to be. We first saw it 10 years ago and we’re still trying to figure out what was real and what was staged.

23. Exit Through the Gift Shop

Widely considered the ultimate concert film, this one captures the Talking Heads at the height of their performative power. Come for the songs, stay for David Byrne’s famously giant suit.

24. Stop Making Sense

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