Photo: William Claxton

The earliest known demo recording of Bob Dylan has hit the auction block. The reel-to-reel tape, that RR Auction in Boston refers to as “Dylan’s earliest demo recording,” captures the then-20-year-old musician delivering a six-song set at the Gaslight Cafe in Greenwich Village on Sept. 6, 1961. The tape and other items that pre-date Dylan’s rise to fame are available via the Boston-based RR Auction. Bidding closes March 12, 2025, at noon local time. 

Dylan played the aforementioned set in front of a 20-person crowd, delivering songs such as “Old Man,” “He Was a Friend of Mine,” “Talkin’ Bear Mountain Picnic Massacre Blues,” “Song to Woody,” “Pretty Polly” and “Car, Car.” The earliest-known recording percolates a four-pack of originals and notes Dylan’s early influence–admiration for the traditionals via “Pretty Polly” and mentor, Woody Guthrie. 

The musician’s then-manager, Terri Thal, said [via the item’s description], “He programmed his set as an audition.” Thal recorded the performance, capturing the early delivery on an Ampex recorder bound in a leather case, placed on a table at stage left, hoping its contents could be used to push future club appearances for the bard. “I didn’t have video… I didn’t have a record. I needed something to show, to play for people to give them an idea of what the guy sounded like.” 

Recounting her history with Dylan, Thal writes in her book, My Greenwich Village: Dave, Bob and Me, “One day in spring 1961, Bob asked, ‘Would you get me gigs?’ Of course I said, ‘I’ll try.’ I didn’t think of asking him to sign a management contract…Bob and I agreed that I would be his manager and would get fifteen percent of any job I got for him, but that I wouldn’t take a commission until he was earning enough to pay me…Getting Bob Dylan work was difficult.”

“Folk singers in New York started to agree with Dave [Van Ronk] and me that Bob was distinctive and remarkable, and that he had great promise. But he didn’t yet have any other audience. Other folk singers went to hear him, but musicians couldn’t constitute enough of an audience to support the cost to a club owner of bringing in a performer,” she recalled. 

While the original Soundcraft Plus-100 box cover panels are included, the tape has been transferred to a fresh Ampex box for preservation. It also comes with the original handwritten tracklist. In addition to the six-song set, the recording also boasts a capture of “Tambornine Man,” which was not performed during the Sept. 6, 1961 gig but added later. 

Bidding is underway, view the listing here.