Bob Dylan’s done it all; some would even say that America’s preeminent songwriter and “song-and-dance man,” as he once called himself, has done too much. Dylan’s recorded some of the finest popular songs in America’s songbook, written unreadable poetry collections, such as the Allen Ginsberg-inspired Tarantula, toured relentlessly for the better part of the last 30 years, and if it that isn’t enough, he’s also dabbled in the visual arts since the early ‘70s. Dylan’s creativity is only matched by his pathological impulse to follow the creative sparks wherever they lead him, which is why he’s written some of the greatest as well as quixotically atrocious songs ever recorded. So much of the pleasure of being a Dylan fan is the musical whiplash his massive catalog induces; one minute, you’ll be cold-cocked by the beauty and tenderness of “Boots of Spanish Leather,” convinced that Dylan is the master of all masters. But then, three songs later, a curiosity like “Tweedle Dee & Tweedle Dum” comes around, and, like the haters and even some elitist Dylan obsessives, you think the man has indeed overstretched.
In my early days of Dylan fandom, when I was enamored with the idea of artistic perfection, I thought that Bob did indeed do too much and that he was ruining his legacy with an imperfect hit-to-miss ratio. But as I enter my second decade as an unabashed Dylanologist, I’m convinced that the man still has more to give. There are many facets to Dylan’s brilliance, but what separates him from mere mortals, and what makes being a fan so enriching, is his willingness to experiment in full view of the public.
Dylan is notoriously private in his personal life, but with his music and other creative endeavors, he lets it all hang out. He releases 15 different cuts of the same song or chops up his masterpieces beyond recognition on tour, his artistic project perpetually shape-shifting like the tides. The artistic “failures,” if you can even call them that — I prefer to call them detours — are often more instructive and pleasurable than a classic such as “Visions of Johanna.” Bob flailing, and trolling, often one and the same, is when he’s at peak Dylan, which is why I’ve followed him down some bizarre artistic alleys — Christmas in the Heart, Masked and Anonymous, etc. — and will continue to do so. I learned long ago not to question where Dylan wants to take us.
So I followed him yet again. This time around, he led me to a museum in suburban Miami-Dade County, where these paintings of his I’ve been hearing so much about for years were being exhibited. “Retrospectrum,” Dylan’s first comprehensive stateside exhibition showcasing his visual art, just finished up its five-month run at the Patricia and Phillip Frost Art Museum on the campus of Florida International University. It’s best described as an uneven marvel. For a Dylan fan, the exhibition is a bounty of brilliance that offers up unprecedented insight into the singer’s long-running obsessions, but the uninitiated will also find much to appreciate in Bob’s oftentimes rudimentary art. The exhibition, which combines six series of Dylan’s work dating back to his earliest sketches in the ’70s, showcases an artist transfixed by archetypal American ideas and images now considered quaint and archaic by those afflicted with “modern sensibilities.” Dylan’s art has deepened and even improved throughout the years. But the diners, bus stops, roadside motels, and other fixtures of the mythology of the open road that represent that most American desire — to get in the car and go — are consistent features. Dylan’s artistic obsessions, as one might expect, run parallel with his musical obsessions.
To be a Dylan fan is to yearn, as Bob does, for that older, weirder America, a long-gone America that you can almost see if you squint hard enough. The paintings might not be consistently excellent, but like Dylan’s finest songs, they tap into our society’s folkways.
The earliest works exhibited are untitled sketches that Dylan painted and published in a book of lyrics titled Writings and Drawings. The black-and-white drawings, mixed media on paper, served as an accompaniment to the lyrics, but like the folk songs Dylan covered in his early days, there’s a gruffness to the childlike renderings that signify the possibility of grander and darker works down the line. The drawings and paintings, much like Dylan’s early musical compositions, are weighed down by a preciousness that he was finally able to purge in later years, when he settled into his final form: no longer the voice of a generation but a living, breathing specter of that old, weird, lost America. If you’ve seen Dylan in the last 20 years, it’s hard to shake the feeling that the curly-haired guy you’re looking at hidden away in the darkest corner of the stage is a ghost.
The early works are followed by the Drawn Blank Series, a collection of colorful, splotchy sketches that Dylan produced while on the road in the late ’80s and early ’90s. The paintings, many of which are acrylic on canvas, highlight random vistas, such as hotel pools, cityscapes, and docks. There’s not much to say about the series other than Dylan discovered color during this era, but like the transitional periods in his musical catalog that serve as bridges between mediocre records and masterpieces, the elements that constitute greatness are present in trace amounts. Two paintings depicting women, Woman Sitting on Floor and Woman on a Bed, capture that spectral quality that would come to signify his late-era records as well as artwork.
In the late ’80s, following a string of commercial and artistic flops, Dylan hooked up with master producer Daniel Lanois and holed up in New Orleans. Dylan, after putting to bed the gospel gimmick that saw him release a Christian trilogy and the embarrassing coked-up rock-‘n’-roller shtick that followed, needed something new to reignite the creative spark. As documented in Dylan’s wonderful autobiographical Chronicles: Volume One, New Orleans, as well as Lanois’s heavily atmospheric production style, reignited the aging troubadour and allowed him to settle into the late-era persona that is seemingly most aligned with the actual Bob Dylan, whoever the hell that is.
Dylan as New Orleanian specter, with Lanois as his guide, created the eerie Oh Mercy, a record that produced the ghostly “Man in the Long Black Coat” and perhaps his greatest breakup song, “Most of the Time.” Oh Mercy, an album haunted by the ghosts of New Orleans and the Mississippi Delta, was a return to form for Dylan. But more importantly, during its production, he became his current and likely final form of himself. The Dylan we see and hear today, the specter, was born in New Orleans. It’s not a surprise then, that Dylan’s finest paintings are found in the New Orleans Series.
The New Orleans paintings, which date from 2010 to 2012, are dark and grimy, depicting loners, dilapidated courtyards, and alleyways. The garish colors of the Drawn Blank Series are absent in the New Orleans Series, but the simplicity of the ’71/’72 early work remains, which translates into Dylan finally finding his artistic equilibrium. For the longtime Dylan connoisseur, the epiphanic moment of realization, in which one understands his creative vision after having listened to a dozen versions of the same song until eventually landing on the “right” version, is where the magic happens. “That’s what he was trying to do all along,” you say, as you listen to an obscure bootleg of “Blind Willie McTell” recorded in a meat locker in Akron. The very same magic is present when one catches a glimpse of the first New Orleans painting. “The old dog can paint, after all,” you think. “The specter is present here in this empty museum,” you think. You listen to all the bootlegs and deal with his mercurial nature at concerts and head out into the western suburbs of Miami for that moment of magic. Keep going, Bob. You haven’t done enough yet.
The Beaten Path paintings, composed from 2015 to 2020, are slice-of-life renderings of the American landscape. The New Orleans paintings are the most formally inventive, playing with space and shadow, but in the Beaten Path series, Dylan is at his most quietly revolutionary. The modern contemporary artist considers classic American tropes and images trite and embarrassing, but Dylan’s paintings, while formally conventional, are imbued with a love and respect for the corners of the country that have long been abandoned not only politically but artistically. There’s no room for a Hooper or a Rockwell anymore, but there’s still 80-year-old Bob Dylan composing paintings with names like Abandoned Drive-In, Yucca Valley, Guthrie’s Alley, Bakersfield — an homage to Woody, of course — and Burger Joint, 12th Street.
Dylan has long been averse to ascribing any meaning or message to his creations, but his late-era paintings, like his best songs, understatedly say it all: The roads still take you to those hidden places where the quiet American magic happens. The donut shop is America. The train station is America. The sad-eyed lady at the bar is America. Bob Dylan gets it. He’s always gotten it.
Alex Perez is a fiction writer and cultural critic from Miami. Follow him on Twitter: @Perez_Writes.

