Book 2 tells the story of Bob Dylan's meteoric rise to stardom.

In January 1961, Bob Dylan arrived in New York City. Within weeks, he traveled to the Greystone Psychiatric Hospital in Morris Plains, New Jersey, to visit Woody Guthrie, who was suffering from Huntington's disease, a progressive degenerative brain disorder. Dylan played songs for him during his visits.

Shortly after his arrival, Dylan made his way to the epicenter of New York's cultural center: Greenwich Village. There Dylan made his name quickly known to the folk community, taking the stage as often as he could at the many basket-houses like the Cafe' Wha?, Gerdes Folk City, and the Gaslight café, where young performers could cut their teeth, earning whatever was in the hat after it was passed around after each set.

Dylan got his first big break on April 11, 1961, when he began a two-week stint opening for bluesman John Lee Hooker at Gerdes Folk City. The gig marked the start of a rapidly ascending career that would see Dylan signed to one of the world's largest record labels within the year.

In September 1961, Dylan arrived at Columbia Recording Studios to contribute harmonica to the music of Texas folksinger Carolyn Hester. Legendary talent scout John Hammond Sr. had seen Dylan perform a fortnight before, and so impressed was he by the young musician that he offered to sign him up for a five-year contract.

In November of that year, Dylan recorded songs for his first album, Bob Dylan, which was released the following year in March. It received little critical notice or commercial sales, yet it was a start. Dylan was now recording for one of the largest and most important companies in the world.

The Freewheelin' Bob Dylan, released in 1963, demonstrated the budding songwriter's distinctive talents with songs like "Girl from the North Country," "Masters of War," and "A Hard Rain's A-Gonna Fall," which remain timeless classics forming the bedrock of Dylan's reputation.

Establishing himself as a new songwriter, Dylan performed for the first time ever on the West Coast at the Monterey Folk Festival in 1963 with Joan Baez singing harmonies, and at the Newport Folk Festival sharing the stage with Pete Seeger and Joan Baez. In October of that same year he performed at Carnegie Hall to a sold-out crowd of thirty-five hundred people, from which a live album was prepared but never released, In Concert.

Dylan's third album, The Times They Are A-Changin', was released in early 1964, and included his most politically overt songs to date. Later that year, Dylan composed one of his most well-known songs, "Chimes of Freedom," a turning point for Dylan lyrically, expanding his style with symbolic and at times fragmented imagery, drawn from his immersion in French symbolist poets and the Beats, some of whom he had just met, such as Allen Ginsberg.