Heylin has written extensively on the life and work of Bob Dylan, combining interviews with discographical research.
Titled All the Madmen, it includes chapters on the Dialectics of Liberation conference of 1967, Syd Barrett, Pink Floyd's album The Dark Side of the Moon, David Bowie's theme of schizophrenia in his songs, the Who's Quadrophenia album, and Nick Drake.
: From Forest Hills to the Free Trade Hall: A Historical View of Dylan's Big Boo.
In 2018, Heylin published his research into Dylan's recording of the Blood On The Tracks album, No One Else Could Play That Tune.
The first of two volumes, this biography is based on research by Heylin in the newly-established Bob Dylan archive in Tulsa, Oklahoma.
Andrew Motion wrote in The Spectator that "Heylin has always been good on this aspect of Dylan’s story — concealment — hence the title of his first biography, and the way this new one repeats an idea of secrecy.