Unlike his prior records this album is mostly his original compositions. Man there is a real loneliness to the sound of these early Dylan records. I've always wondered who that is on the cover with him arm in arm on this frigid New York winter street. She doesn't look like Joan.

Wiki Says: The Freewheelin' Bob Dylan is the second studio album by American singer-songwriter Bob Dylan, released on May 27, 1963 by Columbia Records. Whereas his self-titled debut album Bob Dylan had contained only two original songs, Freewheelin' represented the beginning of Dylan's writing contemporary words to traditional melodies. Eleven of the thirteen songs on the album are Dylan's original compositions. The album opens with "Blowin' in the Wind", which became an anthem of the 1960s, and an international hit for folk trio Peter, Paul & Mary soon after the release of Freewheelin'. The album featured several other songs which came to be regarded as among Dylan's best compositions and classics of the 1960s folk scene: "Girl from the North Country", "Masters of War", "A Hard Rain's a-Gonna Fall" and "Don't Think Twice, It's All Right".

Dylan's lyrics embraced news stories drawn from headlines about the Civil Rights Movement and he articulated anxieties about the fear of nuclear warfare. Balancing this political material were love songs, sometimes bitter and accusatory, and material that features surreal humor. Freewheelin'showcased Dylan's songwriting talent for the first time, propelling him to national and international fame. The success of the album and Dylan's subsequent recognition led to his being named as "Spokesman of a Generation", a label Dylan repudiated. Read more