The generally accepted definition of the word “hipster” in 2017 is a young, non-traditional, counter-culture person who is an independent thinker, believes in progressive politics, and appreciates art and underground music. Typically, it has a pejorative slant. It refers to people who like to think of themselves as trend-setters, but are actually slaves to fashion as much as anyone – if not more so than the rest of us.
The word came into being in the 1920s when jazz first emerged. A whole subculture began to grow around the new style of music and “hip” was the word people used to describe devotees to the new genre. As the scene grew the word entered the common parlance. The word took new form in the 1930s and 1940s. “Hip” got crossed with the word “gangster” to represent a new generation of jazz listeners.
Norman Mailer describes the hipsters of that age as being sidelined African-Americans jazz musicians who lived fast and unconventional lives. This was due to the constant danger they faced at the hands of white supremacists. They tended to live a kind of “gangster” lifestyle to get ahead in a system that was rigged against them. Malcolm X referred to himself in that time as a ‘hipster’ in his autobiography.
In post-war America the meaning of the word expanded again. A new subculture of jazz aficionados known as “the beats” came onto the scene. They were a group of young, scraggly college kids who had deviant tastes in literature and were hip to the underground music of that age, jazz. Writers like Jack Kerouac and Allen Ginsberg surrounded their life with the jazz culture and did everything they could to emulate the spirit of the jazz musicians that they worshipped. Kerouac even made a point of trying to write his stories in a way that paralleled the rhythm of jazz and called his counterparts “children of the American bop night.” They insisted on living in the moment like their African-American counterparts due to the frenzied society they lived in. World-War II was a demoralizing war that showed us the worst in humanity. We witnessed atrocities from the holocaust to the atom bomb. There was a heightened sense of mortality for everyone after that moment. The Beats, who felt this most of all, set out to live in the moment.
Allen Ginsberg described the beat hipsters as “burning for the ancient heavenly connection to the starry dynamo in the machinery of night” in his crowning piece, “Howl.” They sought meaning in a world of conformity. The Beats roamed the country and fought this uniformity everywhere they went. They took pride in being different. They wore drab clothing, had frivolous sex, and amplified their minds with drugs. They didn’t need to live this way; this was a conscious choice. Unlike the African-American hipsters of the Jazz Era, the Beats could conform any time they wanted. They also didn’t limit their counterculture to just jazz. They inspired the world for generations to come by expanding ‘hipsterdom’ to other genres of music, literature, and poetry. They made it a culture. They made it chic. Beats brought spirituality into the mix and encouraged a lifestyle of voluntary poverty: one that rejected materialism, even when it was offered to them.
By doing these things, the hipsters of the Beat generation beget the hipsters of 2017. Though few know it, the hipsters roaming the streets of Wicker Park and Brooklyn emulate the Beats emphatically and sartorially.
 Norman Mailer, “The White Negro: Superficial Reflections on the Hipster,” Dissent, 1957.
 Malcolm X, Alex Haley, and Attallah Shabazz, The Autobiography of Malcolm X: As Told to Alex Haley, ( Ballantine Books, 1992)
 Jack Kerouac, On the Road, ( Penguin Books, 1999)
 Allen Ginsberg, Howl, and Other Poems (San Francisco, CA: City Lights Books, 1986).
In the late spring of 1939, Weldon Kees, his wife Ann, and his parents, John…