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, this album represented the beginning of Dylan's writing contemporary lyrics to traditional melodies. Eleven of the thirteen songs on the album are Dylan's original compositions. It opens with "Blowin' in the Wind", which became an anthem of the 1960s, and an international hit for folk trio Peter, Paul and Mary soon after the release of the album. 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".

Bob Dylan is an American singer-songwriter. Often considered to be one of the greatest songwriters in history, Dylan has been a major figure in popular culture over his 60-year career. He rose to prominence in the 1960s, when his songs "Blowin' in the Wind" (1963) and "The Times They Are a-Changin'" (1964) became anthems for the civil rights and antiwar movements. Initially modeling his style on Woody Guthrie's folk songs, Robert Johnson's blues, and what he called the "architectural forms" of Hank Williams's country songs, Dylan added increasingly sophisticated lyrical techniques to the folk music of the early 1960s, infusing it "with the intellectualism of classic literature and poetry". His lyrics incorporated political, social, and philosophical influences, defying pop music conventions and appealing to the burgeoning counterculture.