
Bob Dylan rose to prominence in the 1960s with songs which were both dazzlingly poetic and adept at capturing the mood of the budding counterculture. In a career spanning more than sixty years, Dylan has been a complex and controversial figure, both loved and hated by his fans at times, and endlessly enigmatic.
Though he’s always drawn and painted, it’s only in the past two decades or so that Dylan has really publicised his visual art, but it’s quickly garnered critical acclaim from around the world. His prints are especially popular, accounting for a staggering 99% of his work sold at auction, where they usually fetch between £1,000 and £5,000, with his Side Tracks series being particularly sought-after.
Despite being in the global spotlight since his early twenties, Dylan has remained fiercely private all his life, and he is notoriously cryptic during interviews. In a way, it doesn’t matter who the ‘real’ Bob Dylan is, since the myth and the man are inexorably entangled, but it is interesting to know some things about him when considering both his songs and artwork. Read on to discover six things you might not have known about Bob Dylan.
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He’s Won The Nobel Prize
In 2016, Bob Dylan became the first musician ever to win the Nobel Prize for Literature “for having created new poetic expressions within the great American song tradition.” The decision was generally applauded, though some criticised it and questioned whether his songs could legitimately be described as poetry.
Never one to make things easy, Dylan did not acknowledge the honour for two weeks, stating later that he “was out on the road” when he received the news, and it took him “more than a few minutes to properly process it.”
His Most Expensive Print Sold For £32,000
Bob Dylan’s most expensive print is from his Side Tracks series, and is titled 18 May 1976, Oklahoma City, Oklahoma. The Side Tracks prints are based on Dylan’s famous Train Tracks image (which is also a print in its own right), and they’re extremely popular in today’s market, accounting for six of his 10 most expensive prints sold at auction.
Each of the Side Tracks prints begins from the same image and is then hand-embellished by Dylan, making every one of them unique. They’re all named after locations and dates of some importance to Dylan, most of which refer to concerts that he played between 1961 and 2013.

He’s On The Never Ending Tour
Bob Dylan was born in May 1941, and he’s now 83 years old; despite this, he shows no signs of slowing down, and he’s been touring pretty continuously for decades. His current touring schedule is popularly referred to as the Never Ending Tour, and it started in June 1988. Many of Dylan’s Side Tracks prints are named after shows from the Never Ending Tour, and to date, he’s played over 3,000 shows since it started, usually performing about 100 concerts a year.
Dylan himself has dismissed the name, asking with his familiar cutting scorn:” Does anybody ever call Henry Ford a Never Ending Car Builder? … Anybody with a trade can work as long as they want. A carpenter, an electrician. They don’t necessarily need to retire.”
He Constantly Reworks His Songs And Art
Dylan is notorious for playing live versions of his songs that sometimes differ so much from the album versions that it’s hard to recognise them at first. He’s always steadfastly refused to be dictated to by the will of his adoring fans, beginning with his rejection of the ‘voice of a generation Messiah’ mantel which was thrust upon him in the ‘60s.
It’s this refusal to settle into anything solid and comfortable that keeps Dylan’s work exciting and interesting after all this time. Songs written more than 60 years ago retain their relevance and their beauty, and Dylan’s constant reinterpretation of them keeps them fresh. In addition to changing the way he plays them, he frequently reworks lyrics, adding and removing verses or changing names and pronouns at will.
This is a practice which has translated to his art, since his Side Tracks prints, for instance, are all variations and reinterpretations of the same image. Moreover, in 2018, Dylan’s Mondo Scripto exhibition in London featured a collection of his handwritten lyrics and accompanying pencil drawings, with many of the lyrics being significantly different from the original album versions. Some of these later became the Mondo Scripto prints, which are extremely popular at auction.

He Has Other Creative Outlets
Dylan is primarily a singer-songwriter, though visual artwork is also a significant part of his creative practice. But he’s also an author, having published one experimental book of prose poetry, Tarantula, and the first part of his memoirs, Chronicles: Volume One (which came out in 2004 – fans have been avidly waiting for the next instalment ever since).
He has also acted, appearing in films such as Hearts of Fire, Masked and Anonymous, and Pat Garrett and Billy the Kid (for which he created the soundtrack). He also directed and starred in the bizarre film, Renaldo and Clara, which is a strange mixture of interviews, concert footage, and fictional vignettes.
He Reinvents Himself
Not only does Dylan constantly reinterpret his work, but he himself is an undefinable, evasive figure who resists categorisation and explanation. Dylan has unabashedly mixed fact and fiction since his first days in New York City, when he excised his middle-class upbringing in a Jewish family in Minnesota, instead claiming in interviews that he’d run away from home and joined a circus during his teenage years.
This love of reinvention has continued ever since. There are, in fact, so many Dylans that in Todd Haynes’ experimental 2007 film, I’m Not There, the musician’s various incarnations and personas were portrayed by six different actors playing different characters.
Dylan’s approach to his own public persona is perhaps best exemplified by what he said upon reading a newspaper story about himself, which claimed he smoked 80 cigarettes a day: “God, I’m glad I’m not me.”