15. Grey Gardens (1975)
Directed by: Albert Maysles, David Maysles, Muffie Meyer, Ellen Hovde
Starring: Edith ‘Little Edie’ Bouvier Beale, Edith Bouvier Beale, Albert Maysles, David Maysles, Brooks Hyers
The Maysles Brothers might be two of the most influential documentary filmmakers in the history of the medium, and 1975’s Grey Gardens might be one of their absolute best, most unique works. The film takes a look at the incredibly odd and hopelessly grungy lives of Edith Bouvier Beale and her daughter Little Edie, the aunt and first cousin of former US First Lady Jackie Kennedy. The very eccentric mother-daughter pair have resided at the titular Grey Gardens estate for decades, the massive home now dirty, cluttered, and dilapidated. Their interactions with each other and with directors Albert and David Maysles are hilarious, unique, weird, and charming in ways I can’t possibly describe in a short blurb about why I adore the film. The Maysles Brothers step back and allow Big Edie and Little Edie to tell their own story throughout the run-time of the documentary, painting a funny and disturbing portrait of this family. The Beale’s many cats (and raccoon’s), their gardener Brooks and other friends of the family, and the Grey Gardens estate feature heavily throughout the film, making it an incredibly memorable experience, and one I can’t possibly recommend highly enough. Grey Gardens is available on Blu-raythrough the Criterion Collection, and I recommend it to anybody interested in the genre.
14. Deep Water (2006)
Directed by: Louise Osmond, Jerry Rothwell
Starring: Donald Crowhurst, Clare Crowhurst, Tilda Swinton
During the painstaking process of composing this list, Deep Water is one of the films I immediately thought of, despite not knowing where or if the film would end up on my list when all was said and done. The fact that the film, which I’ve only seen one time several years ago, made the list is a testament to just how powerful Jerry Rothwell and Louise Osmond’s 2006 documentary is, and the emotional effect it had on me as a viewer. Deep Water tells the story of amateur sailor Donald Crowhurst and his experiences in the 1969 Sunday Times Golden Globe Race, which took a number of yachtsmen around the world for a trophy, a cash prize, and the obvious fame and notoriety that would come with it. Not to spoil things for those who haven’t seen this thrilling doc, but things don’t exactly go entirely smoothly for the amateur seaman, and his trip around the world becomes much more about survival than it does about a measly cash prize. Coupled with archival footage and photos of the time, we get a realistic account of Crowhurst’s time at sea through interviews with those close to him, as well as terrific narration by the incomparable Tilda Swinton. Deep Water is a film that is criminally under-seen in the film community, and could really do with having a resurgence of sorts. Deep Water is exciting, it’s depressing, and it’s incredibly interesting. The film is currently available on US Netflix for those looking to see it based on my recommendation.
13. Inside Job (2010)
Directed by: Charles Ferguson
Starring: Matt Damon
Inside Job is the timely Oscar-winner that took the world by surprise in 2010 by being both incredibly relevant, entertaining as hell, and making more than three times its meager budget at the box office, a rare feat for a documentary. This is especially shocking because it’s not a documentary about a famous person, an iconic or influential movement or artist, but rather about a devastating financial crisis that hit the United States just two years earlier. Inside Job tells the story of how the financial crisis of the late-2000’s took place through five parts: “How We Got Here”, detailing the burst of the internet stock bubble in the early 2000’s, investment banks and other protected corporations and agencies that dealt in things such as unpayable subprime loans, “The Bubble”, which covers the housing boom of the 2000’s, “The Crisis”, about the market collapse of investment banks, the fall of corporations like Merrill Lynch, Lehman Brothers, and AIG, as well as the asset relief program put into effect by US President George W. Bush, “Accountability”, which targets the executives, directors, consulting firms, and others who played a part in the recession, and lastly “Where We Are Now”, about the mass layoffs of American factory workers, and the efforts by the Obama administration to combat the effects of recession. Charles Ferguson’s pressing documentary is insightful, entertaining, and has a hell of a lot to say about those responsible for the market crash. If you’re even the slightest bit interested in important contemporary events that have shaped the Western world, I implore you to check out Inside Job.
12. The Central Park Five (2012)
Directed by: Ken Burns, Sarah Burns, David McMahon
Starring: Antron McCray, Kevin Richardson, Yusef Salaam, Raymond Santana, Kharey Wise
Ken Burns is perhaps one of the most famous names in documentaries because of his epic-length films covering major historical events, wars, and movements. His filmography includes The Civil War, The Dust Bowl, The War, Prohibition, and Jazz. Burns’ 2012 film The Central Park Five is a different monster, quite different from many of his epic historical documentaries. The film covers the famous Central Park jogger case, which saw five young minorities falsely accused and imprisoned for the brutal rape of a female jogger late one Spring night. The assault left the young woman in a coma for nearly two weeks, and resulted in one of America’s most famous cases of false imprisonment. The case was immediately jumped on by news media of the time and involved a great deal of racist implications, finger-pointing, and false accusations being leveled at the five young men. Ken Burns lays all the facts out on the table in the two-hour run-time of The Central Park Five, shocking the audience with accounts of how the defendants ended up in such a dire situation, including stories and evidence of intimidation, lying, and coercement by police officers. Ken Burns’ daughter Sarah joined her father in writing and directing the film, and helped inspire the documentary with her thesis on the cases media coverage. The Central Park Five will move you to tears, infuriate and frustrate you, and make you feel both hopeless and hopeful about the change in direction of news media and law enforcement as a whole. The film is available on Netflix Instant for those interested.
11. Bowling for Columbine (2002)
Directed by: Michael Moore
Starring: Michael Moore
Not only did Michael Moore win an Academy Award for his social-political documentary Bowling for Columbine, but he also made himself an icon in the process; setting the bar for future generations of documentary filmmakers – especially those who wish to eclipse the popularity of their film with their own popularity. Bowling for Columbine is Moore’s heartbreaking, entertaining, and thought and discussion-provoking 2002 documentary that took the world by storm. It was one of the first major pieces of pop-culture to openly criticize the new Bush administration, and started a brand new conversation about gun control and America’s obsession with violence, both in the media, entertainment, and in their political affairs, that is still raging to this very day. The film covers the tragedy that took place at Columbine High School in 2000 in-depth, interviewing some of the survivors of the shooting, features the now famous bank-opening scene, as well as multiple montages and humorous segments covering America’s foreign policy history – installing and overthrowing dictators for fifty years, violent moments in recent American history that the media heavily focused on, and a brief animated piece on the history of the United States and the creation of suburban communities and racism. Though Bowling for Columbine never features a dull moment, the film isn’t all jokes and lightheartedness, it features incredibly eye-opening pieces on the National Rifle Association, the domestic creation of weapons of mass destruction, and the country’s constant obsession with fear-mongering. In short, Bowling for Columbine is a documentary masterpiece in every way, bringing important, valid information to viewers while also being highly entertaining and digestible. Seek it out immediately if you haven’t already seen it.
Part 1 (#20-#16) can be viewed here