It's hard to overestimate the importance of The Freewheelin' Bob Dylan, the record that firmly established Dylan as an unparalleled songwriter, one of considerable skill, imagination, and vision. At the time, folk had been quite popular on college campuses and bohemian circles, making headway onto the pop charts in diluted form, and while there certainly were a number of gifted songwriters, nobody had transcended the scene as Dylan did with this record. There are a couple (very good) covers, with "Corrina Corrina" and "Honey Just Allow Me One More Chance," but they pale with the originals here. At the time, the social protests received the most attention, and deservedly so, since "Blowin' in the Wind," "Masters of War," and "A Hard Rain's A-Gonna Fall" weren't just specific in their targets; they were gracefully executed and even melodic. Although they've proven resilient throughout the years, if that's all Freewheelin' had to offer, it wouldn't have had its seismic impact, but this also revealed a songwriter who could turn out whimsy ("Don't Think Twice, It's All Right"), gorgeous love songs ("Girl From the North Country"), and cheerfully absurdist humor ("Bob Dylan's Blues," "Bob Dylan's Dream") with equal skill. This is rich, imaginative music, capturing the sound and spirit of America as much as that of Louis Armstrong, Hank Williams, or Elvis Presley. Dylan, in many ways, recorded music that equaled this, but he never topped it. ~ Stephen Thomas Erlewine, All Music Guide
The album cover features a photograph of Dylan with his then-girlfriend Suze Rotolo. The photo was taken by CBS staff photographer Don Hunstein at the corner of Jones Street and West 4th Street in Greenwich Village, New York City—just a few yards away from the apartment where the couple lived at the time.<42> The circumstances behind the shoot are described by Rotolo in A Freewheelin' Time: A Memoir of Greenwich Village in the Sixties.<43>