Exclusive: Recently Discovered Early Painting by Bob Dylan Revealed

In the late 1960s and early 1970s, a couple named Sandy and Anthony LePanto lived near Saugerties, New York in a cabin in the woods. When their daughter Aegea contacted me recently, it proved to be an astounding opening into the spiritual and creative world of Woodstock in the late 1960s and early 1970s – and revealed the existence of a very early, and previously unknown, painting by Bob Dylan.

Dylan has been painting since the mid-1960s, and took intensive classes in New York with Norman Raeben in 1974, but most of his canvases are 21st century. Over the past decade, he has done more and more large-scale painting in acrylics and oils, up to his exceptionally fine and critically acclaimed Deep Focus series, based on film scenes and completed during the pandemic of 2020. There are apparently only a handful of paintings, though, from his Woodstock days.

The newly discovered painting, courtesy RR Auction

The best-known is Dylan’s cover art for Music From Big Pink (1968). Others include a portrait of a man in a hat with a guitar, very like the figures on the Big Pink painting, which graced the cover of the October/November Sing Out! magazine; an abstract of a woman that Dylan gave to his manager Albert Grossman and Sally Grossman; and the two paintings on the wall of the Dylans’ Woodstock home, seen in a November 1968 photograph of Dylan and George Harrison, taken by Jill Krementz. The newly found painting is from the same time-period, and Dylan gave it to Sandy LePanto not long after he painted it, half a century and more ago.

Sing Out! magazine cover. Photo credit: collection of the writer

The LePantos moved to the Hudson Valley after they married in April 1967. Anthony worked a variety of jobs around Woodstock and Bearsville, from carpentry to cooking; and he also made jewellery from old coins.

Sandy — born Sandra Burbank in Scottsbluff, Nebraska, in 1944 — was Anthony’s second wife. She was not only one of the most beautiful women in Woodstock at a time when there were many – she was a mystic, an avid student of mythology and ancient sacred sciences, and maker of astrology charts for clients. Mythologies fascinated her, and she read broadly and deeply in the legends of many cultures.

Sandy’s best friend Shelby Scherman Willer remembers when Sandy and Bob Dylan met at the Millstream Tavern, where a harp player named Eve was performing; and again, later at Deanie’s, everyone’s favourite restaurant in town. Shelby herself had first met Dylan in Woodstock through the artist and poet Saul White, who took her to an event at the Dylans’ home. Says 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.”

Sandy did charts for Dylan, and they talked myth and legends, too — he gave her a book, the Larousse Encyclopedia of Mythology introduced by Robert Graves, that Sandy left to Shelby, still her closest and oldest friend, upon her death in 2012. In return for the charts and readings she’d done for him, Dylan also gave Sandy a painting. The old arts community of Woodstock worked on the barter system then, and to a degree does today; people trading their expertise and creative output, rather than paying money.

Shelby recently reflected on this: “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.”

Shelby remembered Sandy’s painting well from the time she first saw it in the LePantos’ cabin long ago. Sandy kept it wrapped it up in a cloth to prevent wood-smoke from the fire that was the cabin’s only heat-source from damaging it; and she was particularly careful of the signature on the back, a charcoaled “Bob Dylan”, embellished with a little swirl of music notes. After Anthony and Sandy separated, Dylan’s painting ended up with Anthony. Aegea told me, “My father took the painting and held on to it for almost five decades. It is in its original condition and frame.”

Sandy LePanto, courtesy of her daughter

In a lifetime of traveling light and relocating often, Anthony never left the painting behind when he moved along. After visiting the area repeatedly from 1971, and shifting from San Rafael to Bolinas and in between, Anthony settled in Woodacre, California, where he was known as Skye. He volunteered for local arts programs and charities, including the local food bank. When he died in the fall of 2023, the painting Dylan had given to Sandy was in his home.

Having talked to people who knew Sandy well, to those who knew both her and Dylan, and who were familiar with the painting from the time when it was given to her, I have no doubt as to its provenance. As to the artist, the style is perfectly late-1960s Dylan, and details are similar to details in his few identified paintings from those days.

The painting is most akin to two other Dylan abstracts from the same time-period: the portrait of a woman in shades of yellow that he did for the Grossmans, which was sold by Julien’s Auctions in late 2021; and one of the two paintings seen in the background in Krementz’s photo of Dylan and George Harrison. One of these, a flat painting of a nude woman on a red chaise, identified as Sara Dylan, was acquired by collector Jeff Gold and is now in the Bob Dylan Center in Tulsa, Oklahoma.

Bob Dylan, abstract, Estate of Sally Grossman, courtesy Julien's Auctions

The other is an abstract that has not, as far as I know, been exhibited or even seen publicly. It is in some points almost identical to the newly rediscovered painting: abstract line images like human profiles and animal figures; the outline of musical instruments and notes; and that stick-figure man in his brimmed hat. The man in the hat is recurrent in most of Dylan’s canvases from the time, mirroring his own style in Woodstock days when he was often seen in a hat with a brim — and functioning very like a self-portrait, or signature.

Unlike the Grossmans’ painting, though, this canvas is signed with an actual signature, on the back. Dylan has written his name in full, together with a string of fanciful music notes in a triangular, shape-note kind of form. He has signed this way before; and the music notes are like those to be found elsewhere in his manuscripts.

The painting is in excellent condition, unvarnished, with no cleaning having trammeled it, and with only a slight loss of the thick white oil paint in a few places. Its underlying colors are earthy greens and browns, as befits its central subject, a bull with sweeping horns. Vivid yellow, orange, coral, and touches of blue make both abstract shapes and recognizable animals, a bow tie, and music notes. The bull’s horns are painted exactly in the sad-banana way of the tusks of the elephant overseeing the figures of the musicians on the Music From Big Pink cover.

Music from Big Pink cover

A fanciful, Picasso-esque face peeks out from the lower centre, the eyes and nose vivid against a green background. The eyes are rimmed with eyeliner, and angled a little — just like Sandy’s. To the left, a small orange deer with antlers echoes the bull; tilt the image a little, and the antlers become music notes. A stick figure in red of a man in a hat, arms outstretched, hovers above and behind the bull like a cowboy or a toreador. There’s a sense of Ernest Hemingway’s writing, of the Hollywood Westerns Dylan evidently enjoys watching and has referred to in songs, as well as of the mythological Taurus — that grounded, earthy sign governed by Venus, and covering most of the month of May.

Detail of eyes and deer, courtesy RR Auction

RR Auctions of Amherst, New Hampshire and Boston are offering Dylan’s abstract in their upcoming May sale. Given Dylan’s current and serious turn back into painting, in acrylics and oils, and the increasing prominence of this artistic medium in his late career, the importance of this new-found painting as one of his earliest known canvases cannot be overstated.

It surely belongs in a museum; which one wins it will be interesting to see.

Sandy LePanto, courtesy of her daughter