Peter Fonda died on August 16 at the age of seventy-nine. Son of Academy Award–winning actor Henry Fonda, brother to actress and activist Jane Fonda, Peter was a celebrated actor in his own right. He will be remembered for his lead role in Easy Rider, the film that is said to capture the Baby Boomer generation’s rebellion against conformity and constraint, and which was released fifty years ago last month. (Ironically, Fonda himself was born in 1940, a few years too early to be a Boomer.) The press release from his family stayed true to the Sixties spirit: “In honor of Peter, please raise a glass to freedom.”

What was freedom? Something that existed in the late 1960s through the early ’70s—or so I’ve been told. During those years, everyone took risks, rent was cheap, hitchhiking was common. As a high-school student, I spent many afternoons listening raptly as my favorite teacher, a scientist and ex-hippie from the Midwest, told stories about hitchhiking races from Kansas to San Francisco. Before the Manson murders, a California professor once told me, you wouldn’t think twice about trusting someone to drive you all the way to Mexico. That was freedom.

The first time I sat down to watch Easy Rider, it was in an attempt to understand that Baby Boomer freedom. “All he wanted / was to be free,” goes “The Ballad of Easy Rider,” the film’s closing soundtrack.* Fifty years since its release on July 14, 1969, the film holds up as a representation of the sense of freedom former hippies talk about. But although producer Buck Henry called it the “automatic handwriting” of the Sixties counterculture, the movie wasn’t only for hippies. The film spoke to mainstream audiences: it was the third-top-grossing film in the United States the year it came out. European moviegoers admired Easy Rider as well, and the movie won the First Film Award (Prix de la première œuvre) at the 1969 Cannes Film Festival. But does cross-cultural appeal in 1969 translate to cross-generational significance in our own time?

To commemorate its fiftieth anniversary, on September 20, Radio City Music Hall in New York will screen Easy Rider and host a concert of the film’s legendary pop-music score, including the Byrds’ Roger McGuinn and Steppenwolf’s John Kay. Fonda’s absence will no doubt weigh heavily on the event, which, according to a press release, is being marketed to Boomers: “Sing along with the songs. Laugh with the humor! Remember the spirit!”

Those of us who weren’t there can take a more critical distance. What was Easy Rider? Is it a time capsule of the Sixties, or a living work of art? Does it still have something to tell us about freedom?

Fonda wrote Easy Rider with Dennis Hopper, a skilled film editor better remembered for his acting, and Terry Southern, the sometime Beatnik who wrote Dr. Strangelove and Barbarella (starring Jane Fonda). Hopper directed the film; Southern conceived of its title, a slang term with many meanings, but which generally connotes a loose, untethered traveler’s existence. Besides Fonda, it stars Hopper and Jack Nicholson, who was then at the beginning of a brilliant career. László Kovács’s cinematography in the film would launch him as a major figure in the “New Hollywood” of the 1970s. Easy Rider is reminiscent of Westerns (with motorcycles instead of horses), but the biker movie was a popular genre unto itself in the Sixties—both Fonda and Hopper had already worked in it before. The hodgepodge of influences generated a conflict between different ideas. There’s no triumphant moment of liberation in Easy Rider, no clear ideology about the meaning of freedom, only clashing images of what freedom might be.

Early on, the scene is irenic, agrarian, even traditional. Having sold cocaine for enough cash to facilitate an early retirement, Wyatt (Fonda) and Billy (Hopper) jump on their customized Harley-Davidson “chopper” motorcycles, and take the road from the American Southwest to Florida. There are beautiful shots of the orange desert; an unblinking, yellow sun; glistening silver motorcycles; an American flag flashing from Wyatt’s leather jacket—all to the sounds of rock ’n’ roll. The heroes stop at the home of a white rancher, his Mexican wife, and their children. Upon learning that Wyatt and Billy are from Los Angeles, the rancher becomes wistful, and tells of how, in his youth, he almost moved to California. But now, look around, he seems to say, I am rooted here. Wyatt admires the rancher’s freedom. “It’s not every man that can live off the land, you know. You do your own thing in your own time. You should be proud.” Next, Wyatt and Billy visit a commune where, notwithstanding countercultural family arrangements, the hippies live a lot like the rancher does. Wyatt and Billy witness planting season. The young back-to-the-land idealists, who recently fled city life, now spread seeds, build scarecrows, and pray. The laconic Wyatt is tempted to stay—but “I just got to go.”

A different view of freedom is embodied in the motorcycles, which enable unrestricted movement, and in the cocaine money, which opens up new possibilities. (The heroes hide their money inside Wyatt’s Stars and Stripes–themed motorcycle gas tank.) Unlike the rancher, Wyatt and Billy are not rooted; they’re always moving forward. But their movement is without a clear direction. Even their final destination seems to be just another stop along the road. They want to make it to New Orleans for Mardi Gras. Later, they want to settle in Florida. But what is Florida, apart from a sunny place apparently beyond the range of an FBI investigation? Even if they don’t get caught, one could imagine Wyatt and Billy parking their bikes in Miami and asking, like Robert Redford in The Candidate, “What do we do now?”

Before they reach New Orleans, Wyatt and Billy stop in Texas, where they meet an alcoholic lawyer named George Hanson (Nicholson), who is somehow affiliated with the ACLU. Hanson adds a political dimension to the film. He bails Wyatt and Billy out of jail, where they landed for “parading without a permit.” He then decides to tag along with the duo, who teach him to smoke pot (they claim it’s a healthy alternative to booze). Hanson warns the travelers that Americans will feel threatened by them, because “of what you represent…freedom.” Americans tend to think they are free but “it’s hard to be free when you are bought and sold in the marketplace.” Through Hanson we become briefly aware of Jim Crow and rural poverty in the South. Yet, broadly speaking, the film’s politics are limited. Women are restricted to supporting roles, while most of the working-class people we meet are depicted as violent persecutors of hippies. Easy Rider is sometimes called a leftist film, but the heroes are primarily interested in their own freedom, not in a political project.

Once they reach New Orleans, Wyatt and Billy visit a legendary brothel, but they seem more interested in death than sex. Two prostitutes accompany them to the Mardi Gras parade and the French Quarter cemetery, where they drop acid amid the whitewashed mausoleums and religious statues. A montage shows the foursome stripping, praying, crying out to absent friends and family. The tension between the modernity of LSD-dropping and the traditional Catholic Mardi Gras parade and cemetery is never successfully exploited. The scene is parasitic on its setting: anything can feel “existential” in a graveyard, and the scene does not get beyond easy atmospherics. The psychedelic trip is presented as a form of mysticism, but it doesn’t reveal anything to the heroes, who after its conclusion keep moving toward Florida, unchanged.

Easy Rider is a lasting work of art not only because it reflects the “spirit of the Sixties,” but because, through memorable images and well-written dialogue, it depicts a bona fide tragedy that transcends its time. Two heroes with a noble desire for freedom encounter various images of it, each enticing in its own way. The rootedness of the farmer, the boundlessness of the traveler, the political rebellion of the lawyer, and the mystery of drugs each have their allure, but all leave Wyatt and Billy hungry. Their search ends in failure and death. Before a bonfire outside New Orleans, Wyatt utters the famously enigmatic line, “We blew it.” They are just about to make it to Florida, flush with cash. But something nags at Wyatt’s conscience. Like all tragic heroes, Wyatt and Billy have somehow missed the mark.

In an interview, Hopper said that “We blew it” was meant to warn that freedom cannot be separated from responsibility. Fonda said that his motivation in delivering the line was his anger at the imperious Hopper, who by many accounts behaved cruelly toward his actors and crew: “Hello, you Fascist fuck, you’ve blown our big chance.” Regardless, the line is an admission of failure: freedom remains elusive.

Wyatt and Billy’s love of freedom isn’t just a Boomer thing. Later generations love it too, even if they often have to express this love in inverted ways. The Millennial experiences of being economically unmoored, or lonely, or incapacitated by a wearying number of “options,” all carry with them a longing for freedom as strong as that of any hippie. That Wyatt and Billy’s search for freedom ends in catastrophe is terrifying, because we’re all afraid that the search will end the same way for us. The heroes are riding off into the sunset. They encounter two men in a pickup truck. One of these men says to the other, “We’ll scare the hell out of them.” But the man in the passenger seat is a bad shot and does more than merely frighten the heroes. Billy bleeds to death and Wyatt’s bike explodes as the camera pulls away. Too many contradictory visions of freedom, in a country geographically vast but crowded with unresolved conflicts and unspoken traumas. Did our heroes ever stand a chance?

*This article originally attributed a line from "The Ballad of Easy Rider" to Bob Dylan. Roger McGuinn has informed us that he is in fact the author of that line.