Rare Abstract Bob Dylan Painting Sells for Over $190,000 at Boston-Based RR Auction

Few musical acts have had as storied a stage career as Bob Dylan. But off stage, far from the cheering crowds, Bob Dylan’s chosen instrument was the paintbrush. And though painting has played second fiddle to his first love, just as he honed his skills of the concert hall, he brought that dedication to the canvas. His classes under seasoned painter Norman Raeben are said to have aided in the narrative development of Dylan’s album ‘Blood on the Tracks.’1 However, few of his earlier paintings have seen the light of day, and are some of the rarest pieces from his past that one can find on the market. But, when one does surface, it can reveal a whole new world of history and color.

In the 1960s and 70s, Dylan became a resident of the small town of Woodstock, New York, where he met up with a local woman named Sandy LePanto. LePanto, born Sandra Burbank, was many things: a mystic, an interested student in the subjects of mythology and ancient sacred sciences, and a plotter of astrology charts. It would be that last facet of LePanto that would spark Dylan’s curiosity. According to Shelby Scherman Willer, Sandy’s oldest and closest friend recalls when Dylan and LePanto first met at the Millstream Tavern while watching the performance of a harp player. 

According to Shelby, “It was not uncommon to have contact with musicians and artists, even those with name-recognition, as they would hang out in local coffee shops, taverns, events or on occasion invite someone to their homes. Sandy made it known in Woodstock that she would prepare astrology charts. It was very popular in those days.”

Dylan consulted Sandy on her talent for charts, and in return for these readings, via the barter system of Woodstock’s art community, Dylan’s talents gave way to his repayment to her, a painting of vivid proportions.

Bob Dylan’s abstract painting from circa 1968, given to Woodstock resident Sandy LePanto.
Bob Dylan’s abstract painting from circa 1968, given to Woodstock resident Sandy LePanto.

Countless motifs can be gleaned from this unique piece. From the hidden music notes, to the red-rimmed eyes in the lower center that – some would say – look just like Sandy’s, to the bow tie on the lower, to the bull that dominates the piece.2

In her retrospective on this time, Shelby said, “Sandy talked about the painting through the years, and how she got it from Dylan in exchange for astrology readings…. I remember seeing the back of the painting. I recall the unique way it was signed with musical bars and notes. The painting itself looked like many abstracts that I had seen from the sixties. Although Dylan is technically a Gemini, he was born in the month of May, so with his early understanding of astrology it is my opinion that he may have thought himself to be a Taurus – the Bull represented in the painting.”

As Shelby describes, Dylan did indeed sign the painting, leaving his maker’s mark on the reverse of the canvas in charcoal accompanied by a sweeping set of music notes.

Dylan’s faintly scrawled signature on the painting’s reverse.
Dylan’s faintly scrawled signature on the painting’s reverse.

To keep the painting safe from the smoke of her and her husband Anthony’s woodfire heated cabin, Sandy kept the painting wrapped in a cloth to prevent damage, taking special care to protect Dylan’s delicate signature. Sadly, the painting would not remain in Sandy’s care, as it would become the possession of her ex-husband Anthony LePanto, where it remained for five decades. After an extended period of travel, lugging the painting along with him, he finally settled in Woodacre, California where he resided until his death in 2023, upon which the painting was rediscovered.

Few of Dylan’s early works have ever been known, much less put on the market, but there have been other rare sightings. Perhaps his best known work from this period is seen on the cover of The Band’s 1968 album Music from Big Pink. Other works have included: his self-portrait for the fittingly titled Self Portrait (1970); an unsigned abstract female nude originally owned by his manager Albert Grossman, which recently sold at auction for $100,000; and two more paintings that are pictured behind a 1968 portrait of Dylan and Beatles alum George Harrison taken by Jill Krementz. One of these paintings, another nude, can be seen by fans at the Bob Dylan Center in Tulsa, Oklahoma, while the other boasts a similar abstract style to Sandy’s prized possession.

Dylan’s painting ‘View from Two Windows’ from his ‘Drawn Blank’ series, depicting an upper story room overlooking a body of water. This painting was previously exhibited at the Halcyon Gallery of London in 2008.
Dylan’s painting ‘View from Two Windows’ from his ‘Drawn Blank’ series, depicting an upper story room overlooking a body of water. This painting was previously exhibited at the Halcyon Gallery of London in 2008.

Dylan’s painting days never faded, but instead gained more focus. From his ‘Drawn Blank’ series, RR Auction sold his 2007 painting ‘View from Two Windows’ for $70,248. Later on in 2016, Dylan partnered with the London Halcyon gallery to exhibit his series of paintings entitled “The Beaten Path.” Featuring, in Dylan’s own words,3 “the American Landscape – how you see it while crisscrossing the land and seeing it for what it’s worth…The attempt was made to represent reality and images as they are without idealizing them…to compose works that create stability, working with generalized, universal, and easily identifiable objects.” A far cry from the unique abstract musings that made up Dylan’s early catalog.

RR Auction’s Marvels of Modern Music closes May 23, 2024, with the winning bid reaching a towering $196,156.

Bob Dylan Exceedingly Rare Original Abstract Painting (c. 1968)

  1. Sam Kemp, “Norman Raeben, the art teacher who changed the way Bob Dylan made music,” Far Out. Published Oct. 16, 2022. https://faroutmagazine.co.uk/art-teacher-who-inspired-bob-dylan/. ↩︎
  2. Anne Margaret Daniel, “Exclusive: Recently Discovered Early Painting by Bob Dylan Revealed,” Hot Press Magazine. Published Apr. 29, 2024. https://www.hotpress.com/music/exclusive-recently-discovered-early-painting-by-bob-dylan-revealed-23020761. ↩︎
  3. Bob Dylan, “In His Own Words: Why Bob Dylan Paints,” Vanity Fair. Published Nov. 2, 2016. https://www.vanityfair.com/culture/2016/11/why-bob-dylan-paints. ↩︎

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