Bob Dylan’s Earliest Demo and Original Paintings Lead $1.18 Million RR Auction Sale
Boston, MA – The earliest known demo recording of legendary singer-songwriter Bob Dylan, captured at New York’s famed Gaslight Café in 1961, sold for $39,325 at Boston-based RR Auction.
The original master demo tape, recorded by Dylan’s first manager Terri Thal, captures a remarkable snapshot of Dylan’s formative stage as a musician. “I didn’t have video—I didn’t have a record,” Thal recalls. “I needed something to show, to play for people to give them an idea of what the guy sounded like.”
Reflecting on her early attempts to promote Dylan beyond Greenwich Village, Thal encountered significant resistance. “In Springfield, the manager wasn’t interested in a new, unknown performer,” she said. “In the thriving folk music scenes of Springfield and beyond, club owners thought Dylan was ‘too freaky’ for their audiences.”
The demo was recorded on an Ampex reel-to-reel machine originally purchased for folk musician Dave Van Ronk. The rare 1/4-inch Reeves Soundcraft Plus-100 tape features six early Dylan tracks, including original compositions “Man on the Street,” “He Was a Friend of Mine,” “Talkin’ Bear Mountain Picnic Massacre Blues,” and “Song to Woody,” alongside traditional covers “Pretty Polly” and “Car, Car.” The recording was digitally transferred by Grammy-winning engineer Steve Addabbo of Shelter Island Sound, renowned for his extensive work on Dylan’s official releases.
“This tape is a revelation—a rare look into Bob Dylan before he was a household name,” said Bobby Livingston, Executive Vice President at RR Auction. “This recording isn’t just a piece of Dylan history—it’s American history, capturing the precise moment when Dylan transformed from a folk unknown into a musical legend.”
Among other notable items sold at the auction, which achieved a total of $1,186,580:
Bob Dylan Original Mixed Media Painting – ‘Cassandra’: A striking nude portrait from Dylan’s acclaimed ‘Drawn Blank Series,’ sold for $79,539
Bob Dylan Handwritten and Signed Lyrics for ‘All Along the Watchtower’: Handwritten lyrics featuring Dylan’s iconic verse, signed neatly at the conclusion “Bob Dylan, 2013,” realized $61,599
Bob Dylan Original Mixed Media Painting – ‘View from Porthole’: An evocative piece from the celebrated ‘Drawn Blank Series,’ achieved $66,448
Bob Dylan Rolling Thunder Revue – Bob Neuwirth’s Stage-Worn Hurricane Carter Benefit’ Nudie Suit’:This elaborately styled ‘Nudie’ suit, purchased by Dylan and worn by Neuwirth during the legendary ‘Night of the Hurricane II’ benefit concert at the Houston Astrodome, sold for $54,206.
Bob Dylan Oversized Signed Photograph (Ltd. Ed. #IV/IV), Royal Albert Hall, 1966 by Barry Feinstein: This exceptional limited-edition print, signed by Dylan, brought $20,788
Bob Dylan Stage-Used Hohner Marine Band Harmonica (European Leg, 1966 World Tour), from the Collection of Barry Feinstein: Dylan’s personally played harmonica from his iconic European tour performances of 1966 realized $19,456
RR Auction’s Fine Autographs and Artifacts sale, featuring these and a variety of additional Dylan-related memorabilia, opened on February 21 and concluded on March 12. For complete results and additional details, visit www.rrauction.com.
