Bob Dylan Traded This Painting in Exchange for an Astrology Reading

A rediscovered painting by musician Bob Dylan is heading to the auction block—50 years after it went missing.

Created around 1968, the untitled piece is one of the self-taught artist’s earliest works. It’s never previously been seen in public. According to the lot listing at RR Auction, it’s expected to sell for as much as $100,000.

The abstract painting is a collage of bold colors juxtaposed with recognizable forms, such as musical symbols, bull horns, bow ties and a pair of eyes. A red outline of a man with a brimmed hat—which some say could be a self-portrait—sits at the top of the canvas.

The singer created the work in Woodstock, New York, while recovering from a motorcycle accident. During this time, Dylan was prolific.

“This period of seclusion capped for the musician an intense spell of touring and a successful run of albums,” writes Artnet’s Min Chen. “At Woodstock, Dylan would write some 100 songs (now collectively known as the Basement Tapes) and, apparently, paint.”

According to the auction house, Dylan created the abstract painting for Sandy LePanto, another Woodstock-area resident. In exchange, she performed astrology readings.

"Sandy was not only one of the most beautiful women in Woodstock at a time when there were many; she was a mystic, a channeler, a reader of stars and maker of astrology charts for her friends,” says Anne Margaret Daniel, a literary scholar and historian who is writing a series of essays on Dylan, in the lot listing. “The old arts community of Woodstock worked on the barter system then, and to a degree still does today; people trading their expertise and creative output, rather than exchanging money.”

Since that fateful trade, the painting has remained with LePanto’s family. It was recently rediscovered in the estate of LePanto’s ex-husband, Anthony Lepanto.

Dylan’s signature is visible on the back of the canvas alongside sketches of musical notes. In the decades since its creation, it has suffered some “minor paint losses” and “flaking,” per the auction house.

The painting will be auctioned during the Marvels of Modern Music sale on May 23. Other items up for grabs include a live recording of Jimi Hendrix playing guitar during a concert with Little Richard, a rare signed photo of Janis Joplin, a typed letter from Jim Morrison and a piano that Prince played on tour.

Other Dylan paintings from around this time have appeared on the covers of albums, such as 1970’s Self-Portrait. As Artnet writes, “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.”

Dylan, now 82, has continued to paint in the decades since. “Many of his paintings were a chronicle of his life on the road, from images of hot dog stands and New York street scenes to paintings of Route 66,” according to the Telegraph’s David Millward. “Very little of his work has ever been displayed, although there was an exhibition of his paintings in Florida in November 2021. It is even rarer for his work to be put up for auction.”

His paintings from the 1960s have fetched high prices in the past. In 2022, an early abstract nude went for $100,000 at a Julien’s Auctions sale, far exceeding its estimate of $20,000 to $40,000.

“The rediscovery of this early painting … represents a signal event in the story of his visual art,” per the lot listing. “The auction of the work offers the rare opportunity to connect with Dylan at the height of his avant-garde creative powers as the 1960s came to a close.”

Julia Binswanger | READ MORE

Julia Binswanger is a freelance arts and culture reporter based in Chicago. Her work has been featured in WBEZ, Chicago magazine, Rebellious magazine and PC magazine.