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Heylin has written extensively on the life and work of Bob Dylan, combining interviews with discographical research. His full-length biography Dylan: Behind the Shades (1991) was republished in a revised second edition as Bob Dylan: Behind the Shades - Take Two (UK edition, 2000) and Bob Dylan: Behind the Shades Revisited (US edition, 2001).
Heylin published a detailed analysis of every song by Dylan in two volumes: Revolution in the Air: The Songs of Bob Dylan: Vol. 1: 1957-73 (2009) and Still on the Road: The Songs of Bob Dylan: Vol. 2: 1974-2008 (2010). These books analyse 610 songs written by Dylan, devoting a numbered section to each song. In 2011, to mark Dylan's 70th birthday, Heylin published Behind the Shades: The 20th Anniversary Edition, which contained 60,000 words of new material to cover Dylan's work since 2000.
Also in 2012, Heylin published E Street Shuffle: The Glory Days of Bruce Springsteen and the E Street Band, a biography of Bruce Springsteen and an analysis of his achievements in the recording studio.
In 2015, Heylin published It's One for the Money, a history of song publishing since the birth of the popular music industry and the establishment of song copyrights at the beginning of the twentieth century.
In 2016, Heylin published his history of UK punk music in the year 1976, Anarchy in the Year Zero: The Sex Pistols, the Clash and the Class of '76.
In October, 2016, Heylin published his study of Bob Dylan's 1966 World Tour, Judas!: From Forest Hills to the Free Trade Hall: A Historical View of Dylan's Big Boo. Heylin has also contributed the liner notes for the 36-CD set, Bob Dylan: The 1966 Live Recordings, released by Sony/Legacy Recordings, which includes every known recording of Dylan's 1966 concert tour.
In 2017, Heylin published his account of Dylan's controversial "Born Again" Christian phase, Trouble In Mind: Bob Dylan's Gospel Years: What Really Happened. The book complemented the release of The Bootleg Series Vol. 13: Trouble No More 1979-1981, which consisted of a large number of out-takes and live performances from this period of Dylan's recording and performance career.