Bob Dylan's earliest known demo recording, made at New York's Gaslight Cafe in 1961, has sold for $39,325 at RR Auction in Boston. The recording, made by Dylan's first manager Terri Thal, represents a crucial moment in music history.

The master tape, recorded on an Ampex reel-to-reel machine, contains six tracks including original compositions "Man on the Street," "He Was a Friend of Mine," "Talkin' Bear Mountain Picnic Massacre Blues," and "Song to Woody," plus traditional covers "Pretty Polly" and "Car, Car." Grammy-winning engineer Steve Addabbo digitally transferred the recording at Shelter Island Sound.

Thal created the demo to promote Dylan beyond Greenwich Village, though she faced resistance from club owners who considered him "too freaky" for their audiences. The recording captures Dylan at a pivotal moment, just before his rise to fame.

Notable Dylan items sold at the same auction included:

• "Cassandra" Mixed Media Painting: $79,539
• Handwritten "All Along the Watchtower" Lyrics: $61,599
• "View from Porthole" Mixed Media Painting: $66,448
• Bob Neuwirth's Stage-Worn Hurricane Carter Benefit "Nudie Suit": $54,206
• Signed Royal Albert Hall Photograph (1966): $20,788
• Stage-Used Hohner Marine Band Harmonica (1966 World Tour): $19,456

The total auction, which ran from February 21 to March 12, achieved $1,186,580 in sales.

"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."

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