Bob Dylan Historian Sean Wilentz on Musician’s Transformation From Imitator to Interpreter

When Bob Dylan arrived in New York City in January 1961, he was a 19-year-old from Minnesota armed with an acoustic guitar and a head full of Woody Guthrie songs. His early recordings from that period — many featured on the just-released The Bootleg Series Volume 18: Through the Open Window, 1956-1963 — reveal a young artist still finding his voice, often mimicking the melodies and vocal styles of his heroes.

Within a few months, Dylan would go through a transformation. The young singer-songwriter became an interpreter of others’ works, imbuing them with a unique character missing on earlier recordings. “The story of Volume 18 is Bob Dylan becoming Bob Dylan,” Sean Wilentz tells Billboard’s Behind the Setlist podcast. Wilentz, author of the 2010 book Dylan in America, wrote Volume 18‘s detailed, often fascinating 125-page liner notes that provides historical context for the expansive eight-CD set. “It’s about his coming of age, his maturation — first as a performer and then as a songwriter — to become the person that we think of [today].” 

With Dylan surrounded by folk, blues, jazz and comedians such as Lenny Bruce, his artistic growth began immediately upon arriving in the Village in early 1961. By the time he was recording his self-titled debut album in November, Dylan had gained an ability to transform somebody else’s song and make it his own. “People will either imitate or they’ll just do a kind of a superficial rewrite,” says Wilentz, a professor of history at Princeton University. Dylan was an imitator when he moved to New York. Just a year later, who would write “Blowin’ in the Wind” and change the course of American music.

Dylan spent these formative months working relentlessly on his craft, writing songs just about anywhere he could. “He can be in the middle of a subway car and he’s writing a song,” says Wilentz. “He’s always writing songs — but he’s doing more than that. He’s learning how to play the guitar. He’s learning how to emote. He’s learning all kinds of things, and he’s working very hard at it. He’s also learning the entire spectrum of American song in a way that most kids just didn’t.”

This wasn’t just artistic growth — it was a metamorphosis. Dylan was no longer mimicking the artists who came before him; he was reshaping songs in his unique style. Wilentz points to Dylan’s recording of the Guthrie’s “Ramblin’ Round,” an outtake that appears on the first CD of Volume 18 as being emblematic of this evolution. “It’s fantastic,” Wilentz says. “You listen to it closely and it’s not Woody Guthrie at all, but it is Woody Guthrie. [Dylan] has turned it into his own song.” “Ramblin’ Round” doesn’t just pay homage — it reimagines Guthrie. Like many of the tracks on Volume 18, it’s a glimpse into an artist who would eventually reshape the American songbook. 

Listen to the entire interview with Bob Dylan historian Sean Wilentz using the embedded Spotify player below, or go to Spotify, Apple Podcasts, Amazon Music, iHeart, Podbean or Everand.