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The Freewheelin' Bob Dylan is het tweede album van Bob Dylan, uitgebracht op 27 mei 1963, drie dagen na Dylans 22e verjaardag. Dit door John Hammond geproduceerde akoestische folkalbum, volgens Rolling Stone Dylans "eerste echte meesterwerk", vestigde Dylans reputatie als liedjesschrijver en belangrijke nieuwe artiest. Het album kwam in 2012 op plaats 97 van The 500 Greatest Albums of All Time van Rolling Stone.

De plaat bevat dertien liedjes, waaronder A hard rain's a-gonna fall, dat op plaats 2 staat in de lijst van 100 beste Dylannummers volgens het blad Rolling Stone. Andere klassiek geworden nummers zijn Blowin' in the Wind, Masters of War en Don't Think Twice, It's All Right.

Er zijn 23 outtakes, waarvan ", "Talkin' Bear Mountain Picnic Massacre Blues", "Let Me Die in My Footsteps", "Rambling, Gambling Willie", "Talkin' Hava Negeilah Blues", "Quit Your Low Down Ways", "Worried Blues" en "Kingsport Town" in 1991 opgenomen werden in de box The bootleg series volumes 1-3.

The Freewheelin' Bob Dylan is the second studio album by the 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".

Dylan's lyrics embraced news stories drawn from headlines about the ongoing 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.

The Freewheelin' Bob Dylan reached number 22 in the US (eventually going platinum), and became a number-one album in the UK in 1965. In 2003, the album was ranked number 97 on Rolling Stone's list of the "500 Greatest Albums of All Time". In 2002, Freewheelin' was one of the first 50 recordings chosen by the Library of Congress to be added to the National Recording Registry for being "culturally, historically, or aesthetically significant".