10 Documentaries About the 1960s That Every Boomer Should Watch

The 1960s was a tumultuous time in U.S. history. There was a lot of change, revolution, and rejection of norms, but for a very long time, cinephiles who wanted to see documentaries about this era were mostly limited to Michael Wadleigh’s 1970 documentary ‘Woodstock,’ which covered the legendary 1969 festival.

Today, Boomers who want to look back on that era have a lot more to choose from. Many talented filmmakers have tried their hand at focusing on one aspect of the decade or another, and thanks to streaming services, you can see most of them right now. Here are our recommendations for documentaries about the 1960s that everyone born between 1946 and 1964 needs to see.

‘The Vietnam War’ (2017)

Directed by Ken Burns and Lynn Novick, this epic 10-episode miniseries dives deep into the complexities and impact of the Vietnam War with personal stories and archival footage. It’s a powerful reflection on a tumultuous period, and it leaves the viewer understanding that this was not a simple war with clear goals or a vision of what “victory” should have meant to the people in charge.

‘Monterey Pop’ (1968)

Documentarian D.A. Pennebaker was fresh off his first feature, “Don’t Look Back,” when he directed this movie, which captured the highlights of the 1967 Monterey Pop Festival. The performances in this movie by Jimi Hendrix and Otis Redding are seminal, and Hendrix’s star-making performance is even better than the one at Woodstock. If somehow, in the past 56 years, you never got around to seeing this movie, you are advised to rectify that post haste.

‘Gimme Shelter’ (1970)

If Woodstock was a depiction of hippie utopia, “Gimme Shelter” depicted the moment it all fell apart. Brothers Albert and David Maysles had filmed the Altamont Free Concert in 1969, a festival organized by the Rolling Stones, expecting it to be peaceful. Unfortunately, the Stones had hired the Hell’s Angels motorcycle gang to do security, which mostly consisted of them beating the crap out of people, ultimately culminating in a fatality. Sociologists can go on and on about when the idealism of the 1960s ended, but the single shot of the woman watching the Rolling Stones and crying during the mayhem tells the whole story in just a few seconds.

‘Summer of Soul’ (2021)

In 1969, the Harlem Cultural Festival, often called the “Black Woodstock,” took place in New York City, featuring performances by Stevie Wonder, Nina Simone, and other Black artists who hadn’t appeared at Woodstock. The whole thing was filmed, but it sat unexhibited for decades until drummer Questlove of the Roots got involved and released it on Hulu in documentary form in 2021 under the name “Summer of Soul.” It’s frankly criminal that this footage went unseen for this long, so turn it on, sit back, and enjoy the music.

‘The Weather Underground’ (2002)

The Weather Underground was a revolutionary organization founded in 1969 at the University of Michigan. Its goal was to create a revolutionary party to overthrow the U.S. government, and they were designated a terrorist group by the FBI. Directors Sam Green and Bill Siegel

tell the story of this group, and even though both of them were too young to remember the events depicted in the documentary, critic Roger Ebert said in his review that “many viewers of the film may discover for the first time how ferociously the war at home was fought.”

‘Crumb’ (1994)

Directed by Terry Zwigoff, “Crumb” tells the story of underground cartoonist R. Crumb, creator of Zap Comix, Fritz the Cat, and the cover of Big Brother and the Holding Company’s record “Cheap Thrills.” Amazingly, while Crumb flies his freak flag openly, he claims to have had no affinity for the hippie movement, saying he hated the music and fell asleep at his lone foray to a Grateful Dead concert. Even more amazing is when the documentary gives screen time to the cartoonist’s two brothers, which reveals that he was actually the most well-adjusted one.

‘1964’ (2014)

Every year of the 1960s was pivotal in one way or another, and you could make a credible argument each could be a standalone topic of their own respective documentaries. This documentary specifically focuses just on the year 1964, which often gets overshadowed by 1963, the year of former president John F. Kennedy’s assassination, or 1968, the year in which Martin Luther King was gunned down. Director Stephen Ives demonstrates that 1964 was no less pivotal, showcasing such politically significant events as the Civil Rights Act and such culturally significant events as the Beatles’ first trip to the United States.

‘The Fog of War’ (2003)

Acclaimed documentarian Errol Morris turns his attention to former U.S. Defense Secretary Robert McNamara, a man who shares plenty of blame for how the Vietnam War was prosecuted. While some might expect him to be a warmongering monster, he proves to be an introspective interview subject, and he has more evenhanded views than one might expect. Oh, and the documentary also reveals that the Gulf of Tonkin incident, which is said to have put the war into motion, was the product of the overactive imaginations of a couple of sailors. Ugh.

‘The Wrecking Crew’ (2008)

You may not be aware of it, but a great many beloved albums from the 1960s were not 100% created by the artists whose names appeared on the album jacket. Much of that music was actually performed by a group of session musicians known in the recording industry as “The Wrecking Crew,” whose work appears on albums by the Beach Boys, Sonny & Cher, and the Monkees. Directed by Denny Tedesco, son of Wrecking Crew guitarist Tommy Tedesco, it’s a loving tribute to the unsung heroes behind many of the 1960s’ most beloved hits.

‘Bobby Kennedy for President’ (2018)

If you weren’t around at the time, you may have some difficulty grasping the gravity of the loss that the country suffered when Robert F. Kennedy was assassinated in 1968 while running for president. Director Dawn Porter gets into the real meat of it and chronicles RFK’s political rise and impact on the 1960s. Boomers, who saw both his ascent and his senseless killing, understand what the nation lost with his death, and “Bobby Kennedy for President” is right there with them to lay it all out in understandable terms both for them and for future generations.