The process of making his first album was very difficult.

Although many people credit Dylan with starting the singer/songwriter era, his debut album didn't have a lot of original songs. Only two of the tracks are actually Dylan originals: "Talkin' New York" and "Song to Woody," the latter of which is an ode to Dylan's idol, Woody Guthrie, whom he met soon after relocating to New York City.

When Dylan began working on his debut album, he didn't have much stability in his life. Even worse, he lacks an abode. Fortunately, he was able to rent his own apartment with the money he made from that CD. Prior to it, he spent the majority of the evening relaxing on the couches of various acquaintances.But he made 161 West 4th Street his permanent home in the West Village using the money from his record deal. The picture that appeared on the cover of his second movie, The Freewheelin' Bob Dylan, released in 1963, was actually taken not far from Dylan's flat.

Dylan and Hammond convened in a Columbia studio in New York City on November 20 and 22, 1961, to record Dylan's debut album. A total of 17 songs, each in a single section and without accompaniment, were recorded by Dylan. In 1962, Dylan remarked, "Mr. Hammond asked me if I wanted to sing a song again, and I said no. "I can't keep singing the same song twice," the speaker said.