NEW YORK - In 1965, a freshly minted recording of Bob Dylan’s “Like a Rolling Stone” was smuggled out of Columbia Records headquarters in New York City and into a downtown nightclub. As the story goes, the single – which was unapproved for release because its electric sound was deemed too heavy and it ran a whopping six-and-a-half-minutes – somehow found its way on to a turntable at the club, where the crowd begged to hear it over and over. Word spread quickly, and soon radio stations were demanding their own copies. Columbia released it as Dylan recorded it, and the song became a smash hit.

bob-dylan-signed-highway-61BOB DYLAN Highway 61 Revisited, Columbia Records, 1965. 12 inch LP
in original picture sleeve, top edge of sleeve splitting. $3,000–5,000

Included on Highway 61 Revisited, Dylan’s sixth studio album, the song has endured as one of rock’s most rousing classics, its thick, layered sound and innovative organ riff instantly recognisable. In his trenchant lyrics, Dylan brings to life a socialite’s riches-to-rags fall. He conjures vivid images like few storytellers in the history of rock and roll have, and rallies listeners each time he belts out the scathing yet heartfelt refrain, “How does it feel?”

That indelible question repeats throughout Dylan’s lyrics, which he wrote out on four pages of stationery from the Roger Smith Hotel in Washington, DC, where he once stayed. The pages are being offered together in Presley to Punk, the first ever sale of rock and roll history at Sotheby’s on 24 June. The personal document reveals the beloved poet’s writing process (doodles and all) and is an incomparably tangible connection to a pivotal moment for rock and roll and for the musician himself. If it weren’t for the song, Dylan might have faded from the music scene altogether. In 1966 he told Playboy magazine: “Last spring, I guess I was going to quit singing. I was very drained . . . But ‘Like a Rolling Stone’ changed it all. I mean it was something that I myself could dig.”

Lead image: Bob Dylan plays piano with a harmonica around his neck during the recording of the album 'Highway 61 Revisited' in Columbia's Studio A in the summer of 1965 in New York City, New York. (Photo by Michael Ochs Archives/Getty Images)

THE ROLLING STONES The Rolling Stones Decca Disques, Promo Poster for the Olympia, Paris, 1965. $2,000–3,000
JIMI HENDRIX Maple Leaf Gardens Concert Poster, Toronto, Canada, May 3, 1969. $1,000–1,500
Elive Presley's Peacock Jumpmsuit. $200,000–300,000
BLONDIE – DEBBIE HARRY Autograph Manuscript of the First Verse of “Dreaming,” Signed by Debbie Harry, circa 1980. $700–900
John Lennon. Upright Piano. $100,000–200,000