Bob Dylan painting from his Woodstock years up for auction – and rare artwork is expected to fetch six figures

A rare painting by Bob Dylan has been put up for auction after he painted the piece during his Woodstock years, around 1968
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One lucky Bob Dylan fan with money to spare is about to score the ultimate piece for their collection.

A rare painting of the folk music legend, whose life is the subject of an upcoming biopic, has been auctioned after he created the piece during his Woodstock years, around 1968, according to RR Auction.

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With a starting bid of $66,550, the auction will run until May 23 and is expected to reach six figures.

Another contemporary painting by 82-year-old Dylan recently sold at auction for $100,000 after he gifted it to his late manager Albert Grossman.

The piece being auctioned at RR is on a 24.5 x 30 inch canvas, with a large outline of a bull, filled with abstract animals, musical notes, bows and other shapes.

A rare painting by Bob Dylan has been put up for auction after he painted the piece during his Woodstock years, around 1968

A rare painting by Bob Dylan has been auctioned off after he created the piece during his Woodstock years, around 1968

With a starting bid of $66,550, the auction runs until May 23 and is expected to reach six figures

With a starting bid of $66,550, the auction runs until May 23 and is expected to reach six figures

With a starting bid of $66,550, the auction runs until May 23 and is expected to reach six figures

At the top of the painting is a red figure wearing a hat that resembles Dylan’s style of that time.

Dylan gave the painting to Woodstock resident Sandy LePanto in exchange for making him an astrology chart.

“Sandy was not only one of the most beautiful women in Woodstock at a time when there were many of them; she was a mystic, a channeler, a reader of the stars and maker of astrological charts for her friends,” wrote Anne-Margaret Daniel in Hot press.

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Sandy’s friend Shelby Scherman Willer recalled: ‘Although Dylan is technically a Gemini, he was born in the month of May, so with his early understanding of astrology I believe he may have mistaken himself for a Taurus – the Taurus represented in the painting.’

The Nobel Prize winner’s signature is faintly visible on the back of the painting, along with scribbles of musical notes.

Although the painting is unpainted and has suffered some wear and tear over the years, 10 bids have already been received on Sunday.

The piece remained in Sandy’s family over the years and was recently rediscovered as part of her ex-husband Anthony LePanto’s estate.

In addition to his groundbreaking music, Dylan is an established visual artist, showing his work in major art galleries around the world and publishing several books of his paintings and drawings.

Dylan’s first painting shown to the public was the cover of The Band’s 1968 album Music from Big Pink.

Dylan gave the painting to Woodstock resident Sandy LePanto in exchange for making him an astrology chart

Dylan gave the painting to Woodstock resident Sandy LePanto in exchange for making him an astrology chart

Dylan gave the painting to Woodstock resident Sandy LePanto in exchange for making him an astrology chart

The auction takes place while Timothée Chalamet embodies Dylan during the filming of the biopic A Complete Unknown in New Jersey

The auction takes place while Timothée Chalamet embodies Dylan during the filming of the biopic A Complete Unknown in New Jersey

The auction takes place while Timothée Chalamet embodies Dylan during the filming of the biopic A Complete Unknown in New Jersey

The Rock and Roll Hall of Famer also painted the covers of his own albums Self Portrait (1970) and Planet Waves (1974).

The auction takes place as Timothée Chalamet embodies Dylan while filming the biopic A Complete Unknown in New Jersey.

Based on the book Dylan Goes Electric! by Elijah Wald from 2015, the film follows Dylan as a 19-year-old who arrives in 1961 New York City.

A Complete Unknown sheds light on his relationship with his hero Woody Guthrie (Scoot McNairy) and other folk music legends, charting his rise to fame and the controversy surrounding his musical change.

The film also stars Monica Barbaro as Joan Baez, Elle Fanning as Sylvie Russo, Edward Norton as Pete Seeger and Boyd Holbrook as Johnny Cash.

Chalamet was cast as Dylan in 2020, when it was announced that James Mangold would direct Jay Cocks’ script, which he rewrote.

Filming began last month after the COVID-19 pandemic and SAG-AFTRA strike boosted production starting in the summer of 2023.

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