18 of the Best Documentaries to Entertain and Enlighten You

The greatest nonfiction films cinema has to offer, from Grey Gardens to Grizzly Man and everything in between.
THE GLEANERS  I CAMERAPERSON WOODSTOCK and GREY GARDENS.
(L-R): THE GLEANERS & I, CAMERAPERSON, WOODSTOCK, and GREY GARDENS.Courtesy of Everett Collection.

Not so long ago, even the world’s best documentaries didn’t do big business. They were considered stodgy, like the vegetables you had to eat as a kid so you’d be allowed dessert. But all that changed in the streaming era, when juicy nonfiction has become one of the most-watched genres. True crime, cult exposés, celebrity profiles, nature frolics, and gripping digests about piping-hot controversies routinely rank among Netflix and Hulu’s most-watched films, and documentarians like Michael Moore, Alex Gibney, and Laura Poitras are as famous to cinephiles as any other director. 

That makes assembling a list of history’s greatest documentaries a fool’s errand. There are so many different types. Do you want to learn about injustices, as in Harlan County U.S.A. and The Invisible War? Do you want a spicy soap opera, like The Tinder Swindler and Three Identitical Strangers? Maybe you’d prefer to revel in beautiful imagery and human feats, as in Free Solo, My Octopus Teacher, and Jane? Or perhaps a fiery political screed, like Bowling for Columbine and the Vietnam War classic Hearts and Minds? How about an eight-hour epic that does it all, à la O.J.: Made in America?

For the purposes of this list, we aimed to include a variety of documentary subgenres that comprise a sample of what the medium can achieve. They’re entertaining and enlightening, stylish and sympathetic. If your favorites aren’t here, that’s simply because there are too many to choose from. 

13th (2016)

13th, (aka THE 13TH), Angela Davis, 2016. Courtesy of Netflix/Everett collection.

After the Martin Luther King Jr. biopic Selma made her a high-profile Oscar contender, Ava DuVernay turned her attention to some of the history that helped fuel the civil rights movement. Formal slavery may have ended when the Thirteenth Amendment was ratified in 1865, but 13th shows how systemic racism instead assumed the forms of political disenfranchisement, segregation, and mass incarceration. Pair it with any number of subsequent documentaries—I Am Not Your Negro and the Hulu series The 1619 Project come to mind—for a vital tutorial in American torment. 

20 Feet from Stardom (2013)

20 FEET FROM STARDOM, (L-R): Jo Lawry, Judith Hill, Lisa Fischer, 2013. By RADiUS-TWC/Courtesy Everett Collection.

Music docs tend to tell the same few stories over and over, so what a treat it is to meet singers who rarely get their own spotlight. Profiling backup vocalists to the hitmakers who sell out arenas, Morgan Neville’s Oscar-winning 20 Feet from Stardom is at once a joyous and heartbreaking look at what it’s like to have proximity to fame. 

Cameraperson (2016)

CAMERAPERSON, Kirsten Johnson, 2016. By Majlinda Hoxha/Janus Films / Courtesy Everett Collection.

Kirsten Johnson has shot some of the 21st century’s most important documentaries, including The Invisible War and Citizenfour. Along the way, she got the idea to make a movie using footage from her globe-trotting cinematography archive. What resulted is a ravishing collage about a life spent behind cameras—the people Johnson has met, the scenery she has captured, the agony and ecstasy she has witnessed. Cameraperson is poetry in documentary form, setting the stage for Johnson’s extremely personal (and charming) follow-up about her aging father, Dick Johnson Is Dead.

The Central Park Five (2012)

The most searing documentary of Ken Burns’s 42-year career is this report he codirected with his daughter, Sarah Burns, and her husband, David McMahon, about the notorious 1989 case that falsely charged five innocent Black and Latino teeangers with raping a white jogger in Central Park (a case later dramatized in Ava DuVernay’s When They See Us). Burns and his collaborators untangle the racist policing and impetuous media coverage that created an imperfect storm all too indicative of America’s worst tendencies. 

Gates of Heaven (1978)

Errol Morris revolutionized true crime with The Thin Blue Line and humanized geopolitical conflict with The Fog of War, but there’s still nothing like Gates of Heaven. Morris’s graceful, philosophical debut, which once prompted Werner Herzog to eat a shoe, is as much about running a homegrown business—in this case, a struggling California pet cemetery—as it is the existential quandary of life and death. Heaven doesn’t have the stylistic excess of today’s documentaries, instead letting its subjects’ unforgettable musings provide more than enough flair. 

The Gleaners & I (2000)

THE GLEANERS & I, 2000. Courtesy of Zeitgeist Films/Everett Collection.

Before polemics like A Place at the Table and Food, Inc. brought attention to the United States’ wasteful food production, Agnès Varda found a slice of lingering agrarianism that exposed her to similar issues in rural France. Gleaning is a centuries-old tradition maintained by a faithful few who, through environmental choice or financial necessity, make use of leftover crops that would otherwise spoil. Without an iota of righteousness, Varda connects their practices to art history, luxe restaurant culture, psychoanalysis, and youthful rebellion.

Grey Gardens (1975)

GREY GARDENS, Edith Bouvier Beale (back left), daughter Edith Bouvier Beale aka 'Little Edie', 1975.Courtesy Everett Collection.

Long before confessionals were a reality TV staple, Edith “Little Edie” Bouvier Beale stood outside her dilapidated East Hampton mansion talking to a camera about her mother’s neediness, her desire to flee home, and her famous “costume for today.” Little Edie was a natural star, and Grey Gardens further popularized the vérité intimacy that brothers Albert Maysles and David Maysles had employed in 1968’s Salesman and 1970’s Gimme Shelter. Much has been made about whether the film exploits or empathizes with its reclusive subjects, but it remains a landmark documentary. 

Grizzly Man (2005)

GRIZZLY MAN, Timothy Treadwell, Amie Huguenard, 2005, By Lions Gate/Courtesy Everett Collection.

Werner Herzog’s metaphysical ruminations have made him one of the world’s preeminent documentarians. He’s chronicled caves, volcanoes, Buddhists, and the internet, but his signature subject matter is a man who communed with bears. Through Grizzly Man’s Timothy Treadwell, a Long Island native who left behind scores of nature footage, Herzog tells the operatic story of an obsession as lovingly animalistic as the ursine creatures Treadwell observed.

The Imposter (2012)

THE IMPOSTER, Adam O'Brien, 2012.By Erik Wilson/Indomina/courtesy Everett Collection.

This stranger-than-fiction saga about a French con artist who convinced a Texas family he was their long-lost relative helped galvanize the true-crime boom that gave us Making a Murderer, The Jinx, Abducted in Plain Sight, Girl in the Picture, and so, so, so many others. The Imposter, directed by Bart Layton, was added to Netflix’s library right around the time the streaming service started premiering original content, boosting the movie’s profile and turning documentaries (especially Netflix documentaries) into major watercooler hits. 

Man on Wire (2008)

MAN ON WIRE, Philippe Petit, 2008. Courtesy of Magnolia Pictures/Everett Collection.

In 1974, when the World Trade Center towers were under construction, eccentric high-wire artist Philippe Petit devised a way to access their roofs so he could spend 45 minutes walking between the buildings via tightrope. Years later, director James Marsh set out to make a documentary about how Petit pulled it off. He had a flash of genius: Petit described his mission as a “coup,” so Man on Wire should be a heist movie. What results is a detailed, suspenseful portrait of human daring, as moving as it is thrilling. 

Madonna: Truth or Dare (1991)

MADONNA: TRUTH OR DARE, Madonna, 1991.Courtesy of Miramax/Everett Collection.

Bob Dylan’s Dont Look Back is often cited as the pop-doc prototype, but the genre’s current ubiquity owes as much—or more—to Truth or Dare. Using some of the same vérité techniques, Madonna and director Alek Keshishian offered an unprecedented look at the coterie of dancers, backup singers, and assistants who kept her famous Blond Ambition Tour running. Today’s musical darlings make glorified press releases and call them documentaries. Few of them have come up with anything as tantalizing, watchable, and self-lacerating as this. 

Minding the Gap (2018)

MINDING THE GAP, 2018. Courtesy of Hulu/Everett Collection.

Bing Liu called Minding the Gap an “American skateboarding story,” a label that’s both precise and overbroad. Skateboarding is the refuge through which Liu and two close friends connected, but the intimate story this young filmmaker tells has more to do with domestic turmoil and the ways childhood strain can harden adults. It’s an extremely American story about class, small towns, and masculinity, but Minding the Gap avoids highfalutin sociology about such topics. This is a human movie through and through. 

Paris Is Burning (1990)

PARIS IS BURNING, 1990. Courtesy of Off White Productions/Everett Collection.

The FX series Pose and the 2016 documentary Kiki have picked up Paris Is Burning’s mantle, but Jennie Livingston’s profile of the late ’80s ball scene remains a seminal work. Slang words like “shade” and “realness” crept into the mainstream partly as a result of this film, a spirited but bittersweet look at a queer subculture that bucks America’s conservative impulses with legendary panache. 

Stories We Tell (2012)

STORIES WE TELL, (L-R): cinematographer Iris Ng, director Sarah Polley, on set, 2012. Courtesy of Roadside Attractions/Everett Collection.

Sarah Polley has two screenwriting Oscar nominations, for Away from Her and last year’s Women Talking, but she also proved to be a masterful documentarian with this memoir about her family history. In excavating her parents’ relationship and its maze of complications, Stories We Tell explores the way perception can alter our sense of reality. Polley’s extremely personal saga plays like a mystery, twists and all.

Weiner (2016)

WEINER, Anthony Weiner (center), 2016.  By Sundance Selects /Courtesy Everett Collection.

Weiner shows a man combusting in real time, and not just any man: Anthony Weiner, one of the most disgraced politicians of our time. This documentary was intended as a comeback story, depicting Weiner’s return to public life after he resigned from the House of Representatives in 2011 for tweeting a lewd photo. Instead, codirectors Josh Kriegman and Elyse Steinberg lucked their way into a real-time account of the subsequent sexual scandals that would further sink Weiner. It’s shocking and—let’s be honest—hilarious. 

Welfare (1975)

WELFARE, 1975Courtesy Everett Collection.

No documentary roster would be complete without Frederick Wiseman, often cited as one of the most important filmmakers alive. His revealing cameras have gone into a hospital for the criminally insane, a primate research facility, Central Park, American Ballet Theatre rehearsals, and the New York Public Library. It’s hard to choose Wiseman’s magnum opus, but 1975’s Welfare is a fantastic place to start. Wiseman uses the New York City welfare system, with its byzantine laws and manifold deficiencies, as a dossier on the United States’ inequity.

When the Levees Broke: A Requiem in Four Acts (2006)

Spike Lee’s nonfiction hasn’t gotten the same attention as his scripted films, with one deserving exception: this four-hour masterwork about Hurricane Katrina. Lee interrogates the numerous government failures before, during, and after the storm that ravaged low-income parts of New Orleans, but his shining achievement is the vulnerability he conjures from locals directly affected. When the Levees Broke, which aired on HBO one year after Katrina, paints a picture of a city under duress, making it essential history. 

Woodstock (1970)

WOODSTOCK, 1970Courtesy Everett Collection

Everyone wishes they’d been at Woodstock, partly because Michael Wadleigh’s documentary so thoroughly captures what the three-day festival must have felt like. Picking up where 1968’s Monterey Pop left off, Woodstock is a hangout movie about a throng of hippies grooving to the sounds of The Who and Jimi Hendrix. The performances are still electrifying today, but it’s the people-watching that elevates this from concert film to historical document. Wash it down with Questlove’s Summer of Soul, about the equally electrifying Harlem Cultural Festival of 1969.