A rare demo recording of Bob Dylan from 1961's Gaslight Cafe in New York has sold for $39,325 at RR Auction in Boston. The tape, recorded by Dylan's first manager Terri Thal, represents his earliest known demo recording.

The 1/4-inch Reeves Soundcraft Plus-100 tape contains six tracks, including four original compositions: "Man on the Street," "He Was a Friend of Mine," "Talkin' Bear Mountain Picnic Massacre Blues," and "Song to Woody," plus two traditional covers: "Pretty Polly" and "Car, Car." Grammy-winning engineer Steve Addabbo digitally transferred the recording at Shelter Island Sound.

Thal originally recorded 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 was made on an Ampex reel-to-reel machine initially bought for folk musician Dave Van Ronk.

Other 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 European Tour): $19,456

The entire auction, which ran from February 21 to March 12, achieved a total of $1,186,580.

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