Heavily inspired by poets like Arthur Rimbaud and John Keats, his writing took on a more literate and evocative quality.
Even when his sales declined in the '80s and '90s, Dylan's presence rarely lagged, and his commercial revival in the 2000s proved his staying power.
On the strength of Peter, Paul and Mary's cover and his opening gigs for popular folkie Joan Baez, Freewheelin' became a hit in the fall of 1963, climbing to number 23 on the charts.
By that point, Baez and Dylan had become romantically involved, and she was beginning to record his songs frequently. By the time The Times They Are A-Changin' was released in early 1964, Dylan's songwriting had developed far beyond that of his New York peers.
Already inspired by Hank Williams and Woody Guthrie, Dylan began listening to blues while at college, and the genre wove its way into his music.
He spent the summer of 1960 in Denver, where he met bluesman Jesse Fuller, the inspiration behind the songwriter's signature harmonica rack and guitar.
By the end of 1964, he had ended his romantic relationship with Baez and had begun dating a former model named Sara Lowndes, whom he subsequently married. Inspired by the British Invasion, particularly the Animals' version of "House of the Rising Sun," Dylan recorded a set of original songs backed by a loud rock & roll band for his next album.