It was a freezing, drizzly night when revellers thronged Times Square to ring in the new year. The following twelve months would go on to be a pivotal era in American history.

1969 had just begun. Massive racial violence continued in the wake of Martin Luther King’s assassination, Nixon was president, the war dragged on. As young people grew more disgusted with the nation’s politics and values, they naturally gravitated towards the counterculture, which promised the conviction that you could drop out of the corrupt mainstream society and live a simpler life, free from religion, capitalism, the nine-to-five, the grey flannel suit and the suburban house with its neat green lawn.

Disenchanted young men and women shunned traditional values and experimented with drugs and communal homes. Some let their hair grow long and left it unwashed. They wore Mexican chalecos, cowboy boots and peasant blouses, they listened to The Beatles and Bob Dylan, they handed flowers to strangers and avoided the draft. As Bruce J Shulman records in his book, The Seventies, the general belief was that “If you could not convince the older generation to change its beliefs, to stop the war, you could refuse to participate”, and that’s what they did. Idealistic and anti-materialistic, they were living an exciting experiment and creating a new, alternative world with no clear course ahead.

Hollywood began capitalising on the growing appetite for rebellion. When Easy Rider premiered in New York on 14 July, 1969, Bowie’s ‘Space Oddity’ was on the airwaves, Nixon had just begun his War on Drugs and Woodstock was one month away. Its themes of resistance and liberation made it an instant hit with the counterculture crowd, and it became the first major motion picture to usher in a new generation of filmmakers who tapped into the radical spirit of the times.

The film traces the journey of two drug-dealing bikers, Wyatt (Peter Fonda) and Billy (Dennis Hopper) as they ride east across America. US road movies depict the wide open highway as a utopian space where characters, free from conventional society, can experience personal transformation – and this breezy sense of liberation was a major part of the film’s appeal.

But it’s not without its sting of existential angst. In Easy Rider, the road appears as a black ribbon of asphalt that stretches out into the shimmering distance before disappearing into a point of bright white on the horizon. Reaching this point is an impossibility, and in the same way, so is the fantasy: those who roam the wilderness don’t have anywhere to go, they just have somewhere they don’t want to be, and all the emptiness reflects a desire to disappear. Wyatt, on his Captain America stars ‘n’ stripes bike folds patriotism and protest into his anguished rebellion but in the end, he becomes a romantic, empty symbol, much like the desert itself.

The cowboy, that other icon of male alienation and rebellion, also made a comeback in the mid 60s. While traditional Westerns from the 50s perpetuated convenient myths about white virtue and Native American savagery; these new, Revisionist Westerns depicted the darker side of traditional narratives and made villains out of those who would be previously considered heroes.

With its tale of two anti-hero outlaw bank robbers, Butch Cassidy and the Sundance Kid (1969) was very much a product of this movement, albeit with one difference that set it apart: the film’s nostalgic, sun-dappled look bucked the revisionist trend for mud, blood and dark moral ambiguity, instead offering a slice of upbeat escapism that appealed to both conservative fans who had grown up with traditional Westerns and the younger counterculture crowd who identified with the anti-establishment protagonists. Like the bikers in Easy Rider, Butch and Sundance weren’t killers, just lovable rebels trying to survive in the world that wants to end their fun.

While many films to come out of the 60s and early 70s depict counterculture values as being at odds with conventional society, others paint the relationship as being more symbiotic. Inspired by and named after Arlo Guthrie’s 18-minute satirical anti-Vietnam war talking blues song of the same name, Arthur Penn’s Alice’s Restaurant (1969) is loosely based on true events that take place in and around a deconsecrated church owned by Alice and her partner, Ray.

Arlo (as himself) is arrested for dumping garbage on the side of the road. He’s called up for the draft where he’s ultimately rejected – not because of his criminal record for littering, but because the government is suspicious of “his kind”. Though critical, the cartoonishly overwrought scenes poke fun at institutional bureaucracy with humour. Coincidentally, Office Obie who arrests Arlo in the film is played by real-life cop Bill Obenhein, who really did take Guthrie to jail. They developed a mutual respect for each other while filming and the two remained friends for the rest of Obanhein's life.

Despite its warmth and sympathetic portrait of both the bohemian community and institutional figureheads, Alice’s Restaurant ends on a minor key. After hosting a big hippie wedding, Ray admits he blames himself for a friend’s death and proposes selling the church and starting a commune. Later, Alice stands on the porch steps in her bedraggled gown, staring into the middle distance as if suddenly realising her married life will be a bleak one. In a 1993 interview with Cineaste, director Arthur Penn revealed the final scene was as comment on the inevitable passing of the counterculture dream: “In fact, that last image of Alice on the church steps is intended to freeze time, to say that this paradise doesn’t exist any more, it can only endure in memory.”

The film captures something essential about that year, especially to the degree in which it depicts disaffected yet optimistic individuals trying, and failing, to create a new community. Unlike the defiant bikers of Easy Rider who meet their demise because they refuse to conform, Alice’s Restaurant sees its protagonists as the unwitting architects of their own downfall, which arrives simply because their version of paradise isn’t sustainable.

In the 60s, it was popular to believe that the situation was rigged – and that sense of hopelessness was part of the appeal. The dream of peace and love was indeed beautiful, yet its allure rested on its fragility and inevitable transience, and movies and music from this decade often captured this bittersweet end-of-an era mood before ending on a downbeat. The artists and filmmakers were right, change was in the air, but the counterculture vision didn’t slip away with a sigh: it exited with a slap that rattled America.

On the morning of August 9, 1969, a man called the police after finding five people dead in a Beverly Hills home. There was a blonde woman on the living room floor with stab wounds in her swollen belly. There was a corpse wearing a hood, another behind the wheel of a car, and two more on the lawn. The word ‘pig’ was smeared in blood on the white front door. Cult leader Charles Manson had directed his followers to break into a ranch rented by the film director Roman Polanski, where they killed his pregnant wife, Sharon Tate, and four guests. A second set of murders took place the following night.

For many, the killings were an articulation of their fear of America’s hippies, hustlers and rebels who represented the underbelly of society. For members of the counterculture community, it was a violent realization of their vision: Manson took the concept of free love and inverted into something sinister and deadly. The sentiment never quite recovered, and if there is one moment that defines the end of an era, this is it. As Joan Didon wrote in The White Album, her 1979 book of essays, “Many people I know in Los Angeles believe that the 60s ended abruptly on August 9, 1969.”

Even today, the murders have a morbid hold on the public’s imagination. Emma Cline’s 2016 bestseller The Girls chronicles the summer of a 14 year-old protagonist who leaves her family to live on a ranch with a group of teenagers all devoted to a Manson-esque man named Russel. Similarly, Director Quentin Tarantino’s Once Upon a Time … in Hollywood, which premiered at Cannes in May 2019, explores Los Angeles in 1969 through the fictional friendship of an actor and his stuntman who happen to live next door to Tate and Polanski.

If the Manson murders sounded the revolution’s death rattle, The Altamont Free Concert was the nail in the coffin. On December 6, The Rolling Stones held a disastrous music festival in California that descended into considerable violence, including three accidental deaths and the murder of Meredith Hunter who was stabbed by a member of the San Francisco Hell’s Angels. The 1970 documentary Gimme Shelter chronicles events as they unfolded, though filmmakers were criticised for staging an ill-prepared event that should never have happened, while portraying the Stones – who wanted to profit from having a ‘concert film’ – in too sympathetic a light.

Altamont took place just months after Woodstock, a three day event 400,000 people attended – far more than were anticipated, far more than organisers could feed and care for. It rained, there was gridlock, dogs and children ran wild, and yet the music continued. People cooked together, got high together, slept together. But while the latter fuelled the hope that a new society had been created, the former was, according to Rolling Stone in a 1970 article “...the product of diabolical egotism, hype, ineptitude, money manipulation, and, at base, a fundamental lack of concern for humanity.” Later, in Esquire magazine, Ralph J. Gleason claimed, “The day The Rolling Stones played there, the name became etched in the minds of millions of people who love pop music and who hate it as well. If the name ‘Woodstock’ has come to denote the flowering of one phase of the youth culture, ‘Altamont’ has come to mean the end of it.”

The efforts to create a cultural revolution began to collapse. Communes disbanded, counterculture magazines foundered, hippy culture became commodified and watered down, and by the winter of 1969, the mood had shifted. Sydney Pollack’s breathtakingly bitter They Shoot Horses, Don’t They? depicts a winner-take-all Depression-era dance marathon in which the contestants danced until they dropped for the chance to win a $1,500 cash prize. The dancers can leave whenever they want, and yet they become increasingly despairing, unable to stop the gruelling charade while the spectacle-hungry crowd gazes on. The deep pessimism reflected a generation’s realization that its most cherished hopes would not be met, and that it would finally have to confront the dark realities of the era.

By the early 70s, a Fortune poll revealed nearly half of college students thought they were living in a “sick” society and films from the beginning of this new decade, such as Five Easy Pieces (1971), Two-Lane Blacktop (1971), Vanishing Point (1971), and Electra Glide in Blue (1973) dripped with this sense of disillusionment. Later, in 1987, Bruce Robinson captured the bitter ‘end of an era’ bleakness with his film Withnail & I which, while not a direct product of either the era or the country, perfectly captures the mood.

The film opens in a squalid flat in Camden Town, London. Watery winter light filters through grease-smeared windows, picking out detritus in the gloom: dusty wine bottles, piled newspapers, spilling ashtrays and a kitchen sink crowded with filthy plates. It looks like a room the morning after a big, messy party. Except in this case, it’s a decade’s worth of parties. Withnail, the title character, is an unemployed actor whose alcoholic, raging eloquence lends him an air of elegance, but his glamour rests on his ability to remain one beat away from ruin, which, in the end becomes unavoidable. As Danny, his local drug dealer, neatly concludes: “They’re selling hippie wigs in Woolworths, man. The greatest decade in the history of mankind is over. And as Presuming Ed here has so consistently pointed out, we have failed to paint it black.”

Danny was partly right. Hippie culture was not what many of its contemporary interpreters would like it to be: the community was made up of predominantly middle class kids who adopted the fashions and listened to the music without truly following the alternative lifestyle or making any kind of political statement. For many, it was only ever about the aesthetic, the drugs and hanging out – and when you look at it this way, its eventual commodification and failure seems inevitable. It’s tempting to assume the end of this dream was wholly bleak, but while 1969 turned increasingly violent and reactionary, it was also a progressive and productive year.

The Supreme Court struck down legalized segregation and discrimination, record numbers of black voters were registered in states across the country and Moneta Sleet, Jr. became the first African-American to win a Pulitzer Prize in Photography. Meanwhile, inspired by the continuing black protests and the anti-war movement, young people started to demand queer and trans rights. The Stonewall riots, which began on June 28, birthed the beginnings of gay liberation. It wasn’t the first riot, nor was it the last – but it did make the most noise: immediately afterwards, activists spread leaflets and zines throughout New York’s East Village, spurring three more demonstrations. A year later, the first pride march took place.

Mainstream films also began reflecting this cultural shift. When Midnight Cowboy came out on 15 October 1969, it was the first X-rated picture to win an award. It was originally given an R rating, which was changed to an X due to its “homosexual frame of reference” and its “possible influence upon youngsters”, and then changed back again. The shuffle is, as Scott Tobias noted in The Guardian, interesting because it tells us “...something about Midnight Cowboy as a watershed moment in the culture, marking a transitional period where Hollywood was responding to radical social change, but not quite keeping up the pace”.

That’s not to say the movie is a bastion of gay rights, love and culture in the way that Fellini’s Satyricon or Toshio Matsumoto’s radical Funeral Parade of Roses are – both of which also premiered in 1969. The fact the Stonewall riots took place a month after its release was purely coincidental, and its coy depictions of male hustle on Times Square are mired in desperation. “If our faux cowboy had wanted to have sex with men,” The Guardian’s Scott Tobias concludes, “the film might have kept its X.” What Midnight Cowboy does do is ask its audiences to sympathize with marginalised characters, and they did: it went on to win three Oscars at the 42nd Academy Awards.

People look back on this year and lament the loss of innocence, but innocence also represents an idealised vision that does not tally with the complexities of reality. It’s touching to see films that capture the full flowering of the hippy moment in all its youth and longing, but it’s the downbeat movies produced during this decade and the beginning of the next one that evolve a commentary on changing societal issues.

Standing on a steep hill in Las Vegas in 1971, journalist Hunter S. Thompson once recalled the feelings of change he had felt a few years earlier: “that sense of inevitable victory over the forces of Old and Evil. Not in any mean or military sense; we didn’t need that. Our energy would simply prevail … We had all the momentum; we were riding the crest of a high and beautiful wave … So now, less than five years later, and with the right kind of eyes you can almost see the high-water mark – that place where the wave finally broke and rolled back.”

Those who wanted change in the 60s may not have achieved everything they set out to do. But, like a wave, the era did leave something behind, something valuable: a newly mature, realistic American society better prepared to process and address the complexities of the world. Though it would have a long way to come yet.

Once Upon a Time… in Hollywood, directed by Quentin Tarantino, is in UK cinemas from the 14 August