A painting by musician and self-taught artist Bob Dylan, newly rediscovered after more than 50 years, is headed to auction, where it is estimated to fetch $100,000. Previously unseen, the untitled work emerges from his Woodstock years and represents one of his earliest stabs in the medium.

The ca. 1968 canvas is an abstract swirl of earthy tones—greens, browns, oranges—set off by forms such as bull horns, musical symbols, and a pair of eyes. A red stick figure wearing a wide-brimmed hat sits at the top of the painting. On its reverse, Dylan signed the work alongside a sketch of musical notes.

Detail of an untitled painting (c. 1968) by Bob Dylan. Photo: RR Auction.

Dylan created the work at a time when he was ensconced in his Woodstock, New York property following a motorcycle accident. This period of seclusion capped for the musician an intense spell of touring and a successful run of albums that included 1966’s Blonde on Blonde. At Woodstock, Dylan would write some 100 songs (now collectively known as the Basement Tapes) and, apparently, paint.  

The work coming to auction was created by Dylan for Sandy LaPanto, a resident of the Woodstock area, in exchange for some astrology charts and readings. According to writer Anne Margaret Daniel, who contributed to the 2023 book Bob Dylan: Mixing up the Medicine, LaPanto was “a mystic, a channeler, a reader of stars, and maker of astrology charts for her friends.” She added: “The old arts community of Woodstock worked on the barter system then… people trading their expertise and creative output, rather than exchanging money.” 

Detail of an untitled painting (c. 1968) by Bob Dylan. Photo: RR Auction.

The painting remained in LePanto’s family for over five decades before it was rediscovered as part of Sandy’s former husband Anthony LePanto’s estate. The Boston-based RR Auction will sell the painting as part of its Marvels of Modern Music sale on May 23. 

“Bob Dylan’s visual art, like his music, draws from a deep well of cultural and personal expression,” said Bobby Livingston, the auction house’s executive vice president, in a statement. “This painting from his Woodstock years is particularly evocative, capturing the vibrant and transformative spirit of the ’60s.”

Detail of an untitled painting (c. 1968) by Bob Dylan. Photo: RR Auction.

Dylan’s other paintings from this period can be seen on the covers of the Band’s 1968 album, Music From Big Pink, and his own 1970 record, Self-Portrait. Two of his abstract canvases can also be glimpsed in the background of photographs shot by Jill Krementz when George Harrison paid Dylan a visit at his Woodstock home in 1968.

Little else, however, is known about Dylan’s early works. So, when they do show up at auction, they show up in a big way. In 2022, an abstract nude that he painted for his manager Albert Grossman in the 1960s made $100,000 at a Julien’s Auctions sale. By way of comparison, the auction record for Dylan’s latter-day works was set by a 1991 sketch of train tracks, which fetched £41,600 (about $52,200) at Roseberys London last year. 

Other highlights from RR Auction’s sale include a previously unheard live recording of Jimi Hendrix in concert with Little Richard, a typed letter the Doors’s Jim Morrison wrote to musician Tony Glover, and Prince’s stage-used Yamaha grand piano.