Neal Cassady was one of the most prominent personalities of the post-World War II literary movement - 'Beat Generation’. He had a rough childhood, after he lost his mother at the age of ten, which left him under the uncaring eyes of his alcoholic father. His early teenage life was very troubled, with arrests for a number of petty thefts, which finally led to his imprisonment. After Cassady came out of jail, he went to New York, where he became acquainted with members of the ‘Beat Generation’, Jack Kerouac and Allen Ginsberg. Though he did not enjoy much of a writing career himself, Cassady’s wild lifestyle, magnetic energy and high spirit inspired many of his writer friends. Jack Kerouac's novel 'On the Road' is inspired by his travels and features a character that is modelled after him. There have been numerous works of literature, films and music that have been inspired by his life. Unfortunately, he became a victim of drug abuse and led a rather carefree lifestyle. A complicated soul, Cassady’s sexual exploits, obsession with drugs and hedonistic life made it difficult to fulfil family obligations.