The Great Sex Letter

On March 7th of 1947, a drunken Neal Cassady — the man on whom Dean Moriarty in On the Road would later be based — wrote the following letter to his friend, Jack Kerouac, and described two recent sexual encounters. Cassady’s uninhibited, free-flowing prose was a huge influence on Kerouac’s writing and this letter in

Come on now Marlon, put up your dukes and write!

Late-1957, with his newly released novel attracting near-universal praise from critics, Beat author Jack Kerouac aimed for the sky and wrote the following passionate letter to Marlon Brando in an effort to bring his work to the big screen. The novel in question was On the Road, and Kerouac — desperate to capitalise on the incredibly

Burroughs has gone insane

Early 1957, Jack Kerouac and Allen Ginsberg travelled to Tangier to join William Burroughs; their mission to assemble and edit Burroughs’ many fragments of work to form a ‘readable’ Naked Lunch manuscript. Kerouac arrived early and, during a break from socialising with Burroughs, the ‘old familiar lunatic’, wrote to Lucien Carr and his wife Francesca in order to update them on

I am Adam and I’m alone again with all my ribs intact

The following letter, written by Jack Kerouac in 1962 following an apparent escape from New York’s many temptations, is predictably fascinating and equally saddening. Over the course of just three pages addressed to Jacques Beckwith, Kerouac manages to touch on his general ill-health, his many troubled relationships with women (most notably then-girlfriend Lois Sorrell), the