Bob Dylan Painting from his Woodstock Years up for Auction

The canvas is filled in with captivating abstract shapes and patterns combined with recognizable imagery, including music notes, bow ties, animals, and segmented features. At the top is the red outline of a man in a brimmed hat—mirroring his own style during his Woodstock days (consider the 'Nashville Skyline' album cover)—which, as writer Anne Margaret Daniel has noted, functions as something of a self-portrait.

Dylan's painting techniques range from thin background layers to thick impasto, with bright yellows, corals, and oranges juxtaposed against more earthly base layers of greens and browns. The painting is signed faintly on the reverse, "Bob Dylan," with musical notes sketched below. Stretched over a wooden strainer with fixed joints, the work is unvarnished and exhibits some undulation, minor paint losses, and flaking; a complete condition report is available at RRAuction.com.

This remarkable artwork was presented by Dylan to a Woodstock-area resident, Sandy LePanto, in exchange for making an astrology chart. Writes Daniel: "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. Mythologies fascinated her, and she read broadly and deeply in the legends of many cultures....Dylan gave Sandy a painting in exchange for the charts and readings she’d done for him. 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." The painting has remained in the family since that time, and was recently rediscovered as part of Sandy's ex-husband Anthony Lepanto's estate.

Very few of Dylan's early works are known, and even fewer have been offered at auction. The most famous of his paintings from this time period is the cover art for The Band's 1968 album Music from Big Pink, featuring wide swaths of solid colors in the guitars, faceless figures, and, as Daniel observed, an elephant with tusks that quite resemble the bull's horns in the present work. His self-portrait for Self Portrait (1970), executed using a similar impasto technique, is stylistically similar—flat in the Fauvist mode, with visible brushstrokes—although less complex. Recently, an unsigned abstract female nude done by Dylan in the 1960s, executed in a similar palette and owned by his manager Albert Grossman, was sold at auction for $100,000. Two other paintings of his are seen in the background of Jill Krementz’s November 1968 portrait of Dylan and George Harrison: one, a nude, today resides at the the Bob Dylan Center in Tulsa, Oklahoma; the other, accomplished in a similarly abstract manner, boasts the 'man in a hat' motif.

Bob Dylan's visual art reflects a similar depth and complexity as his song lyrics, revealing the boundless nature of his creative spirit. In recent years, Dylan has continued to work as a visual artist, and is particularly well-known for his 'Drawn Blank' series—a visual autobiography capturing his life on the road—his 'Mondo Scripto' illustrated lyrics, and the critically acclaimed 'Deep Focus' paintings, completed during the pandemic. The rediscovery of this early painting—one of Bob Dylan's earliest known canvases—represents a signal event in the story of his visual art, and 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.

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