A Rare Sixties-Era Bob Dylan Painting Is Up for Auction

In the summer of 1966, shortly after the release of his acclaimed seventh studio album Blonde on Blonde, Bob Dylan was in a motorcycle accident just outside Woodstock. The musician would spend a few years recuperating in the New York town, where he recorded songs and dabbled in painting.

Dylan has since become more involved in visual art, with comprehensive exhibitions including a 2019 show at Shanghai’s Modern Art Museum that showcased more than 250 of his works. But paintings from the songwriter’s initial foray into painting during the 1960s are rare, with examples rarely heading to auction. Now, a rediscovered work created by Dylan while he was living in Woodstock in 1968 is being sold by Boston’s RR Auction in an online auction concluding on May 23. The painting, which has an estimate of more than $100,000, currently has a top bid of nearly $130,000.

The Woodstock era

When Dylan resided in Woodstock, the town’s vibrant artistic community often used the barter system. His painting, for example, was gifted to local resident Sandy LePanto in exchange for astrological services. LePanto was “a mystic, a channeler, a reader of stars and maker of astrology charts for her friends,” according to the writer Anne Margaret Daniel, who wrote an essay for the 2023 book Bob Dylan: Mixing up the Medicine.

The painting for decades remained in LePanto’s family and was recently found in her ex-husband’s estate. Combining earthy greens and browns with bright corals and yellows and signed by Dylan on its reverse side, the piece’s imagery includes musical notes, animals, a large bull head and even a red outline of a man in a brimmed hat. The latter reflects Dylan’s own look during that era, as evidenced by his style on the cover of the 1969 album Nashville Skyline.

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A similar “man in hat’ motif can be seen in one of the two Dylan paintings pictured in the background of a 1968 Jill Krementz portrait of the musician and George Harrison at his Woodstock home, alongside a nude that is now in the collection of the Bob Dylan Center in Tulsa, according to RR Auction. Dylan’s most well-known work from his time in Woodstock, meanwhile, adorned the cover of The Band’s 1968 album Music from Big Pink and depicted faceless figures playing instruments.

In part due to their rarity, his earlier works have been known to fetch high figures when offered to the public. In 2022, an unsigned female nude from the 1960s gifted by Dylan to his manager Albert Grossman realized $100,000. RR Auction’s offering, which already surpassed that sum, will be sold alongside lots like an original 1965 recording of Jimi Hendrix with Little Richard and a stage-used grand piano from Prince’s final tour in the auctioneer’s Marvels of Modern Music sale.

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