The painting, which dates back to around 1968, was crafted during Dylan's time in Woodstock, New York. This period was significant for the rock icon, as he was collaborating with The Band. Their recordings from this era were later released in 1975 on The Basement Tapes and in 2014 on The Bootleg Series Vol. 11: The Basement Tapes Complete.

RR Auction described the artwork as a "colourful and energetic abstract composition." The painting features the large outline of a bull at its centre, surrounded by abstract shapes and patterns. It also includes recognisable imagery such as music notes, bow ties, animals, and segmented features. Notably, the top of the painting has a red outline of a man in a brimmed hat, reflecting Dylan's own style during his Woodstock days.

According to RR Auction, Dylan exchanged the painting with Woodstock resident Sandy LePanto in return for an astrology chart. The painting remained in LePanto's family until it was rediscovered in her former husband Anthony LePanto's estate.

Anne Margaret Daniel, an expert on Dylan, noted that Sandy was a mystical figure in Woodstock, known for her beauty and her skills in astrology. "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," Daniel wrote. "Dylan gave Sandy a painting in exchange for the charts and readings she’d done for him."

Beyond his music, Dylan is also celebrated for his artistic talents. One of his paintings was featured on the cover of The Band’s 1968 debut album, Music from Big Pink. His artwork also adorned his 1970 double album, Self-Portrait.

"Dylan's artistry knows no bounds, evident in this vibrant piece that melds music, symbolism, and personal reflection," said Bobby Livingston, RR Auction’s executive vice president, in a statement. "With his 83rd birthday upon us, this sale highlights the enduring impact of his multifaceted talent."

Currently, Dylan is on tour as part of the 2024 Outlaw Music Festival, which also features Willie Nelson, Robert Plant, Alison Krauss, and John Mellencamp.