3. Jack Kerouac and On the Road

It’s unsurprising that the Beat Generation — a group of free-thinking people who wanted to be free of normalcy, rejecting the conformity of a nine-to-five job paired with a gray flannel suit — found themselves flocking to artsy places like San Fransisco and Greenwich Villiage. The Beat movement, named by Kerouac and John Clellon Holmes in 1948, was led by authors Jack Kerouac, William S. Burroughs and Allan Ginsberg, who met in New York City at Columbia University. The movement largely revolved around authors, but the idea of breaking free from the norm caught on after Kerouac published On the Road in 1957.

The Beat Generation talked and wrote about the subjects that were taboo in the ’50s like sex, drugs, alcohol, and prostitution. One of the biggest beatnik ideas was the concept of never being tied down to the degree that you couldn’t just pick up and leave if you wanted to. On the Road centers around a group of friends who follow their every whim; they pack bags and spend three years trekking around the country on bus rides. While the characters are frequently on-the-go, Dean Moriarty lives in New York City for the largest period of time when they’re not traveling across the country.

Kerouac’s On the Road was written on a single scroll of paper. Narrator Sal Paradise was meant to emulate Kerouac; Carlo Max as Allen Ginsberg; Old Bull Lee as William S. Burroughs and Dean Moriarty as Neal Cassidy. Kerouac, like the characters in his novel, frequently traveled around the country in a similar fashion, seeking writing inspiration and freedom. Kerouac struggled with setting up the novel and finding a style he liked, but his writer’s block went away after he received a letter from Neal Cassidy illustrating a crazy weekend Cassidy had had. Kerouac later decided on a freeform journalistic style of writing that he dubbed “spontaneous prose.

Kerouac and his beatnik friends spent enough time in New York City to have a long a long list of frequent haunts, many of which no longer exist today. Harmony Diner, the diner that the men are seen entering in the short, silent video, is gone; Cedar Tavern closed in 2008, and Hector’s Cafeteria, where the beats consumed a whole lot of glazed cakes and cream puffs, shut down too long ago to find a date. “Men do love bars and good bars should be loved,” Kerouac wrote in his autobiographical work, Lonesome Traveler. That was a sentiment shared by most of the beats and the few beat haunts still standing today are bars, which would undoubtedly make Kerouac happy if he were alive to see it.