The 10 Best Beatnik and Countercultural Hippy Icons That Defined a Generation

1. Ken Kesey and the Merry Pranksters

Ah, Ken Kesey, one of the most iconic countercultural figures to grace the Beat Generation of the 1950s, and the hippies of the 1960s. Kesey is famous primarily for two main reasons: drugs and writing. He authored the classic classroom text One Flew Over the Cuckoo’s Nest. The inspiration for this book came while working nights at the Menlo Park Veteran’s Hospital. Set in an Oregon psychiatric hospital, the narrative studies institutional processes and the human mind. He spent a lot of time talking with patients at the hospital and came to believe they were not insane, but that society pushed them out because they were unconventional. The novel, upon release in 1962, gained immediate critical and commercial success.

His interest in a wide selection of psychoactive drugs first began when he volunteered to take part in Project MKULTRA. This project, also located at the Menlo Park Veteran’s Hospital, studied the effects of psychoactive drugs. In particular, the study focused on LSD, magic mushrooms (psilocybin), mescaline, cocaine, DMT and AMT. During his time here Kesey wrote many detailed accounts of these experiences. Of course, these also helped frame the book One Flew Over the Cuckoo’s Nest.

After his time as a medical guinea pig, Kesey moved to the private use of drugs. Kesey became notorious for hosting wild parties that came to be known as Acid Tests. Along with his followers, dubbed the ‘Merry Pranksters’, he integrated the consumption of LSD with live music to throw some epic parties. These parties further combined strobe lights, black lights, fluorescent paint, and songs from artists such as the Grateful Dead designed to heighten the sense and widen the mind.

In 1964 Kesey and the Merry Pranksters also embarked on an epic cross-country road trip in a school bus. Along the way, the group attempted to experience roadway America while high on LSD and create art out of everyday life. Of course though, with every great drug story, there comes a dark side. In 1965 police arrested Kesey for possession of marijuana. Kesey then faked his death in an attempt to get out of a drug charge. He had his friends leave his truck on a Cliffside road and left a long suicide note. Meanwhile, he fled to Mexico in the back of a friend’s car. When he returned to the United States eight months later, the courts sentenced Kesey to six months in the San Mateo County Jail. Upon his release, he moved back to Oregon and continued to write short stories, books, and articles.

In 1998, health problems, including a battle with diabetes and a stroke, began to weaken Kesey. In 2001 Kesey had surgery to remove a tumour on his liver. Unfortunately, he failed to recover from the operation and he died on the 10th November 2001.

2. Allen Ginsberg

As a writer and poet, Irwin Allen Ginsberg is frequently considered to be one of the leading figures of the counterculture movement in the 1960s. He embodied various aspects of the counterculture, from his views on drug-use, openness to Eastern religion, and his hostility to bureaucracy. He also opposed sexual repression, militarism, and economic materialism.

Allen Ginsberg’s love life caused a great deal of controversy in the United States. He had relationships with several men but also had a lifelong partner named Peter Orlovsky. His poem, “Howl”, particularly caught the attention of the press. In it, Ginsberg denounced conformity and the destructive forces of capitalism in the US. However, the poem’s description of homosexual sex did not go down well in some circles and became the subject of an obscenity trial. At the time, homosexual acts were a crime in every US state. Fortunately, however, Judge Clayton W. Horn ruled the poem was not obscene.

Ginsberg remained very active in protests against the Vietnam War. He signed the anti-war anti-draft manifesto “A Call to Resist Illegitimate Authority” in 1967. In 1968 he also signed the “Writers and Editors War Tax Protest” pledge, refusing to pay tax in protest against the atrocities of the Vietnam War.

One of the more unusual acts he participated in involved the so-called ‘levitation of the Pentagon. In October 1967, anti-war protesters marched on the Pentagon to ‘levitate’ the building “300 feet in the air” (according to Abbie Hoffman). Ginsberg himself deemed it a success: “the Pentagon was symbolically levitated in people’s minds in the sense that it lost its authority which had been unquestioned and unchallenged until then. But once that notion was circulated in the air, and once the kid put his flower in the barrel of the kid looking just like himself but tense and nervous, the authority of the Pentagon psychologically was dissolved.” Speakers followed the event with a variety of anti-war speeches and poems.

What happened to Allen? Well, in 1960 doctors treated Ginsberg for a tropical disease; it is thought he contracted hepatitis at this point. In the 1970s, he then suffered two minor strokes diagnosed with Bell’s palsy. Muscles on one side of his face consequently drooped. In 1996, after returning home from the hospital where they had unsuccessfully tried to treat his congestive heart failure, he made phone calls to friends and family to say goodbye. Apparently, even Johnny Depp received a phone call. He died on the 5th April 1997 after succumbing to liver cancer via complications of hepatitis. He was seventy-years-old.

3. William S. Burroughs

Born in 1914, William S. Burroughs grew up to become one of the primary figures of the Beat Generation and a major postmodernist author and artist. Overall, he wrote eighteen novels, six short story collections, and four collections of essays. Burroughs was a very well-educated man. In 1932 he studied English at Harvard University; he then studied anthropology as a postgraduate at Columbia, and medicine in Vienna. He, like many of the men famous in this era, engaged in homosexual intercourse and became a part of LGBT culture.

Burroughs’s life was deeply affected by drugs. He enlisted in the U.S. Army in 1942. The Army classified him as a 1-A Infantry rather than an officer and he became dejected. His mother got Burroughs a civilian disability discharge after acknowledging his depression. Shortly after the Office of Strategic Services and the Navy rejected him, Burroughs picked up a drug addiction. As a heroin addict, he lived throughout London, Paris, Mexico City, and Tangier in Morocco. Much of his work is semi-autobiographical and based on these experiences. He found his first major success with his confessional novel, Junkie (1953) but is best known for his third novel, Naked Lunch (1959).

While living in New Orleans, the police arrested Burroughs for heroin possession. The police then searched the home he shared with his wife and unearthed letters from Allen Ginsberg. In these letters, the men discussed a possible shipment of marijuana. The potential implications of this revelation were grave. It is highly likely he would have to serve time in Louisiana’s infamous Anglo State Prison. Consequently, in 1950 he fled to Mexico City to wait out the length of his charge’s statute of limitations.

In 1951, while living in Mexico City, Burroughs accidentally killed his second wife, Joan Vollmer. Though he later changed his story and claimed the gun accidentally fired when he dropped it, the initial line was that he shot her with a pistol during a drunken round of the “William Tell” game. He attempted to shoot a water tumbler off her head but missed and hit her. After returning to the United States, a Mexican court convicted Burroughs in absentia of manslaughter. He received a two-year suspended sentence.

Despite all this, or maybe in spite of all this, Burroughs is often called one of the most influential and greatest writers of the twentieth century. Burroughs died in 1997 after suffering a heart attack at his home in Lawrence, Kansas. He only had one child, William S. Burroughs Jr., but he sadly died before his father. In fact, in 1981 William Jr. died aged thirty-three as a result of alcoholism and liver failure.

4. Timothy Leary

Timothy Leary was an American psychologist and writer best known for exploring the potential of psychedelic drugs under controlled conditions. Most famously, during the period in which LSD and psilocybin (better known as magic mushrooms) were legal in the United States, he conducted experiments under the Harvard Psilocybin Project. In this project, started in 1960, Leary worked alongside Aldous Huxley and others to study the effects of psilocybin on human subjects. As the study progressed, Allen Ginsberg shared Leary’s enthusiasm and the two wanted to help people “turn on” to discover a higher level of consciousness. Together, they introduced several intellectuals and artists to a variety of psychedelics.

It was in March 1962, when the project first became an issue. Members of the Centre for Research in Personality believed drug experiments were being conducted in an irresponsible and unscientific manner. Leary and Alpert pledged not to give drugs to undergraduates, and the Massachusetts Food and Drug Division ruled that drugs could be administered only in the presence of a physician. By May 1963, both Leary and Alpert left Harvard. Harvard allegedly fired Leary for failing to give his required lectures and absenting himself from the university area without permission. Meanwhile, Harvard fired Alpert for giving psilocybin to an undergraduate in an off-campus apartment.

Leary adamantly believed that LSD showed great potential for therapeutic use in psychiatry. He populated some of the phrases that characterised the 1960s: “Turn on, tune in, drop out”, “set and setting”, and “think for yourself and question authority”. He also advocated other psychedelic drugs as well as marijuana. Leary, funnily enough, also created the “Leary biscuit”! A briefly microwaved snack cracker with cheese and a small bud of marijuana. He objected, however, to drugs that he believed dulled the mind. This included morphine, heroin, and heavy alcohol use.

Leary most certainly held some interesting views on drugs and their effects. In September 1966, in an interview to Playboy magazine, Leary claimed that homosexuals could use LSD to cure their ‘disease’. Later, however, he changed his view and no longer characterised homosexuality as an illness in need of a cure.

During the 1960s and 1970s, the police arrested Leary so often that he saw the inside of thirty-six prisons worldwide. His first arrest came in December 1965 when the police arrested him for possession of marijuana. Like many other figures in the era, he ran away to Mexico. On their return, officials found marijuana in his daughter’s underwear. Leary took responsibility for the controlled substance and found himself sentenced to thirty years in prison, psychiatric treatment, and a fine of 30,000 USD. Over time, courts sentenced him to prison again and again, and he continued to escape. In a 1969 court case Leary v the United States, Leary successfully appealed his 1965 case. The Supreme Court ruled that the Marihuana Tax Act of 1937 unconstitutional as it required self-incrimination. This overturned his 1965 conviction. Sadly, Leary died in January 1995 after doctors diagnosed him with inoperable prostate cancer.

5. Jack Kerouac

Jack Kerouac, born Jean-Louis Kérouac, was a famous novelist and poet. Alongside the aforementioned William S. Burroughs, and Allen Ginsberg, historians deem Kerouac a pioneer of the Beat Generation. His most recognisable writing method is spontaneous prose. He covered a wide range of topics in his writings, from Catholic spirituality to travel to jazz to Buddhism, drugs, and poverty (to name a few).

In his youth, Kerouac surprisingly won scholarships for his skills as a running back in football. He earned offers from Notre Dame, Boston College, and Columbia University. He chose to attend Columbia, however, he broke his leg during his freshman season and his football career was over. He consequently dropped out of university but continued to live in New York’s Upper West Side. It was here that he met the likes of Burroughs, Ginsberg, Cassady etc.

Kerouac joined the United States Merchant Marine in 1942, and it was here that he wrote his first novel, The Sea Is My Brother. However, it was not published until 2011. He also joined the Navy in 1943 but this did not last long. A few weeks in, doctors diagnosed him with a schizoid personality and resultantly honourably discharged him on psychiatric grounds.

Kerouac actually pioneered the word ‘Beat Generation’ in 1948. He used the term to characterize the underground, anti-conformist youth movement in New York. Kerouac admits the term ‘beat’ came from fellow novelist Herbert Huncke. Huncke used the term to describe a person with few prospects and little money; a man tired or beaten down. However, Kerouac altered the meaning to include more positive connotations such as “beatific” and “upbeat”.

Kerouac completed his most famous book, On the Road, in April 1951. It was first published, however, by Viking Press in 1957. Kerouac based the story on his travels with friends across the United States. It tells the tale of their experience with jazz, poetry, and drug use. He chose to tell the story as if writing a letter to a friend. Using his favoured writing method, spontaneous prose, he believed the letter form reflected the improvisational fluidity of the jazz music dominating the era. Many publishers refused his work as they felt uncomfortable with the graphic descriptions of homosexual behaviour and drug use within it.

Sadly, Kerouac died at only forty-seven years old in October 1969. Owing to a lifetime of heavy drinking, he died from an abdominal haemorrhage. His family buried him in his hometown at Edson Cemetry in Lowell, Massachusetts.

6. Aldous Huxley

Aldous Huxley is surprisingly older than popular perception believes. Born in 1894 in Godalming England, he helped inspire many of the figures spoken about in this list. Huxley was a very well-educated man and attended Eton College before gaining a place at Balliol College at the University of Oxford. His most notable works include The Doors of Perception, Brave New World, Island, and The Perennial Philosophy.

In 1937, Huxley moved to Los Angeles with his wife, son, and friend. It was here, in the circles he ran, that he solidified his persona as a humanist, satirist, and pacifist. He also grew increasingly interested in spiritual subjects such as philosophical mysticism, and parapsychology. Furthermore, he grew to be a very charitable person. He earned a lot of money as a screenwriter and used a lot of it transport left-wing and Jewish artist and writer refugees from Hitler’s Germany to the USA.

In the spring of 1953, Aldous Huxley had his first experience with psychedelic drugs. The first drug he used was Mescaline, a hallucinogenic comparable to LSD and magic mushrooms. Dr Humphry Osmond, a British psychiatrist, supervised Huxley. Huxley hoped that using these drugs could expand consciousness and lead to a greater degree of awareness and enlightenment. He believed drugs could break down the barriers of the ego, and draw man closer to spiritual enlightenment. Huxley recounted his experience that afternoon in his text The Doors of Perception, published 1954. A great read by the way!

In 1937 he moved to Los Angeles and remained there until his death in November 1963, aged sixty-nine. He died the same day as author C. S. Lewis. Both of their deaths, sadly, were overshadowed by the assassination of John F. Kennedy the same day. Huxley’s ashes are in a family grave in the Watts Cemetery, in Compton, Surrey, in England. He has left his legacy in literature in a variety of ways. Stunningly, throughout his life he has been nominated for the Nobel Prize in Literature nine times; sadly, however, he never won. In 1939, however, he received the James Tait Black Memorial Prize. In 1959, he received an American Academy of Arts and Letters Award of Merit for Brave New World. Finally, in 1962, the Royal Society of Literature made him a Companion of Literature.

7. The Beatles

Ok ok, so technically not a single individual, but still important in contributing to the countercultural and hippy movement. When the Beatles arrived in a pre-countercultural America, their long hair attracted more comments than their music. Part of the hippy movement rebelled against preconceived societal norms, and the Beatles helped spur this on.

The group also mocked gender distinctions that characterized the American landscape. They questioned those who believed sexuality hinged on difference and instead blurred the lines between genders and expanded possibilities. This rang true in particular when it came to fashion and hairstyle. It was not generally acceptable at this time for boys to have long hair, toss it over their shoulders, or to wear colourful clothing that stood out from a crowd.

The Beatles also helped to bring greater awareness to many social-political changes in both the United States and abroad. The Beatles, just liked most hippies, professed ideas of free love, freedom, civil rights, gay rights, pacifism, and ecology. Members of the Beatles were also characterized with fervent anti-war attitudes. John Lennon, for example, released a song titled ‘Imagine’. The single encouraged listeners to imagine a world without barriers, borders, or the divisions of nationality and religion, as well as a world without attachment to material possessions.

The Beatles also changed attitudes to sexuality and helped pave the way for the sexual revolution. The Beatlemania craze that swept the nation had girls screaming and fainting, abandoning control and protesting the sexual repressiveness and rigid double standards of female teen culture.

Most famously, of course, the Beatles also used several of drugs that hippies used too. The Beatles’ were turned on to marijuana by none other than the famous Bob Dylan. In August 1964, the two parties gathered in a hotel room in New York and Dylan rolled a joint to share with the group. They spent the next few hours getting high, forever changing the music they would go on to produce. Interestingly, it is alleged the group were first introduced to LSD by a dentist who slipped it into their drinks at a dinner party in 1965. This influenced much of their work to come. Their song ‘Day Tripper’ is about an LSD trip, while ‘Lucy in the Sky with Diamonds’, literally spells out LSD.

8. Abbie Hoffman

Abbot Howard Hoffman, better known as Abbie Hoffman, was an American social and political activist, anarchist, and revolutionary. Like many of the others on this list, he was a writer, activist, and psychologist. He studied a B.A. first in psychology at Brandeis University. He then undertook a master’s at the University of California, Berkeley, also in psychology. Along with four friends, he co-founded the Youth International Party, known more commonly as the Yippies.

The Yippies, founded in December 1967, were a radical youth-oriented countercultural revolutionary offshoot. Members tended to be either denounced or ignored by many of the ‘old school’ political left. Further, much to the annoyance of many New Left members, the public often perceived the Yippies as the same as the New Left. Though there were some similarities, members of each were also countercultural figures, for example, there were political differences. The Yippies believed in free-speech and anti-war movements but were also more anti-authoritarian and anarchist in their approach than the New Left.

The Yippies were heavily into combining theatrical gestures and politics. In 1968, for example, they advanced a pig (named “Pigasus the Immortal”) as a candidate for President in order to mock the status quo. Further, members planned a six-day Festival of Life in Chicago at the same time as the Democratic convention. They promised the festival would be a “blending of pot and politics into a political grass leaves movement – a cross-fertilization of the hippies and New Left philosophies.” Talking of theatre, they threatened (albeit in a tongue-in-cheek way) to put LSD into Chicago’s water supply.

After protests at the so-called Festival of Life became violent, and monumental clashes with the police ensued, police arrested Abbie Hoffman over his role in organising the protests. The courts tried seven other men too in a heavily publicized case that became known as the Chicago Seven. His charge? Conspiracy to incite rioting. Though the defendants were initially convicted, on appeal the courts overturned their verdicts.

In 1980 doctors diagnosed Hoffman with bipolar disorder. Hoffman died in 1989 aged fifty-two. The coroner ruled his death a suicide as he swallowed one-hundred-and-fifty phenobarbital tablets as well as liquor. A life-long friend of his believed he was unhappy about reaching middle-age. This was made worse by the fact that the ideology he strongly supported in the 1960s gave way to the conservative backlash in the 1980s. He believed the youth was not as socially active or interested in protesting and became disillusioned with the times he lived in.

9. The Brotherhood of Eternal Love

Again, not so much an individual person as they are a group, the Brotherhood of Eternal Love was an organization of drug users and distributors. The group, founded by John Griggs as a commune in the mid-1960s, lasted through to the 1970s and resided primarily in Orange County, California. They became self-sufficient and grew their own crops, built their own hopes, and wove their own clothes. In doing so, they created their own version of society. They also became known as the Hippie Mafia because they hoped to kick-start a psychedelic revolution in the United States.

Religion was a central part of the Brotherhood. They believed LSD offered a window into God and would act as a key to unlock the “Doors of Perception” (a reference to the aforementioned Aldous Huxley’s book). The group began to distribute LSD named Orange Sunshine, a brand they invented themselves. Several members travelled directly to Kabul and Kandahar via Karachi, Istanbul, Frankfurt, and London to gain hash to help fund the distribution of LSD. It was a huge global operation with drugs stashed in a variety of locations such as inside hollowed-out surfboards. Note, you can read more about these specific adventures in a book by Nicholas Schou named Orange Sunshine: The Brotherhood of Eternal Love and Its Quest to Spread Peace, Love, and Acid to the World.

In 1970, the Brotherhood hired the militant radical left-wing organization Weather Underground. The Weather Underground (more commonly known as the Weatherman), wanted to create a revolutionary party that could overthrow the United States. The Brotherhood, however, hired them for twenty-five-thousand dollars to help Timothy Leary who was serving a five-year sentence for marijuana possession. After Leary climbed over the prison wall, the weatherman smuggled him out of the prison in the United States and assisted him in fleeing to Algeria.

Sadly, their fun came to an end in August 1972. Police conducted a drug raid and arrested dozens of members in Maui, Oregon, and California. In 1994 and 1996, police arrested even more members of the group. As late as 2009, police were STILL arresting members! The last was Brenice Lee Smith. He pled guilty to a single charge of smuggling hashish from Afghanistan to Orange County. In return, the District Attorney’s office in Orange County dropped all other charges against him. He spent two months behind bars then returned to his daughter and wife in Nepal where he lived for thirty-years prior.

10. Bob Dylan

Born Robert Allen Zimmerman, Bob Dylan is an American singer-songwriter, painter, and author. Born in Minnesota in 1941, Dylan had a tremendous impact on both popular music and culture. In the 1960s he became the voice, albeit reluctantly at times, of the generation. A lot of his lyrics incorporated philosophical, political, social, and literary references. He used these to challenge the accepted beliefs of American society.

Generally, Dylan used his music as a form of protest and to raise awareness of injustice in the United States. Songs such as “The Times They Are a-Changin” and “Blowin’ in the Wind” became influential in the anti-war and Civil Rights Movement. Further, ‘a song titled ‘The Death of Emmett Till’ also became particularly powerful among many Civil Rights Movement protestors. This song highlighted the plight of a young black man killed by members of the Ku Klux Klan in 1955. Despite some white men confessing to their crimes, a jury found them innocent. Bob Dylan uses this case to show how entrenched the Jim Crow era still was and that injustice needs to be acknowledged.

Dylan’s political profile rose in May 1963. He wrote a song called “Talkin’ John Birch Paranoid Blues”, criticizing the far-right fringe group named the John Birch Society (JBS). Mocking the group, a paranoid narrator in the song is convinced that communists are infiltrating the country and begins to search in all manner of places to route it out. CBS, however, informed him the song was potentially libellous to the John Birch Society and so could not be aired. Rather than comply with this level of censorship, Dylan refused to appear on the Ed Sullivan Show that evening.

His third album, The Times They Are a-Changin’ showed a more cynical and politicized Dylan. After a few more albums, and a huge wave of success, Dylan grew tired of being in the spotlight. In July 1966 he crashed his motorcycle in New York. To date, the extent of his injuries remain unknown but Dylan himself stated: “trust was that I wanted to get out of the rat race”. Following this crash, he withdrew from public view. Though he continued to release music and made a few public appearances, he did not tour again for nearly eight years.

Overall, Bob Dylan has led a very successful life. When it comes to awards, he has won eleven Grammy Awards, an Academy Award, and a Golden Globe Award. In 2008, the Pulitzer Prize jury awarded him a special citation for his “profound impact on popular music and American culture, marked by lyrical compositions of extraordinary poetic power”. President Barack Obama awarded Dylan the Presidential Medal of Freedom. Last, but not least, in 2016 he won the Nobel Prize in Literature for “having created new poetic expressions within the great American song tradition”.