The Story of Jack and Neal

The friendship that made On the Road—and the Beat Generation possible

- By James Parker. Illustration by Oliver Munday

What are friends for?

For knocking around with, cracking a joke, sharing a doobie, firing a paintball? Or for guarding in the angelic citadels of their being the essential soul image of you and everything you might eternally come to mean, while you in shining symmetry and perfect vulnerability do the same for them?

The time has come for me to write a full confession of my life to you,” Jack Kerouac typed thunderously to Neal Cassady in December 1950, in the first of a sequence of massive, rumbling-and-rolling autobiographical letters, steeped in memory and mystery, that he would mail from Queens, New York, to San Francisco. “Bullshit is bullshit. Everything's got to go this time. No one can take it but you. From the very start, we were brothers.” Cassady at the time was supporting a young family by working as a brakeman on the Southern Pacific Railroad; Kerouac was in retreat, annoying his new wife, Joan; brooding over the poor sales of his big, Thomas Wolfean debut novel, The Town and the City; trying and failing to find a new voice/style/idiom/rhythm in which to project his own experience, and the flavor of his distinctly bruised consciousness, more immediately onto the page. Despite grave auto-examinations, it wasn't happening: false starts, loose ends, quarreling selves. His next book-working title: Gone on the Road—had been trapped in a state of unbecoming.