Despite its easygoing title and cozy cover photo, The Freewheelin' Bob Dylan saw the artist growing, deepening, and darkening his daunting songcraft. It's a Musicheads Essential Album.

Although his vast promise as a singer-songwriter landed Bob Dylan a major label record deal at age 20, the young man from Minnesota wasn't an overnight success. His 1962 self-titled debut failed to chart in the U.S., and Columbia Records talent scout John Hammond had to argue with his colleagues to give Dylan another shot.

Dylan's resulting sophomore release, The Freewheelin' Bob Dylan, made more of a commercial impact when it was released in 1963, but most importantly it demonstrated his peerless skill as a songwriter. It's not an exaggeration to say that nearly half the tracks on the 13-song release became not just famous, but iconic.

The folk scene was in awe of how Dylan squared the circle of contemporary protest music with songs like "Masters of War" and the era-defining "Blowin' in the Wind," then on top if it delivered timelessly bittersweet love songs like "Don't Think Twice, It's All Right" and a composition looking backward to a youthful romance, "Girl from the North Country."

The song that pointed the way forward for Dylan, though, was the surreally apocalyptic "A Hard Rain's a-Gonna Fall." It was taken as a response to the Cuban Missile Crisis, but the eerie lyrics were far less specific than that, encompassing not just the Cold War but the entire unsettled state of the human race.

Few albums have transformed an artist's career as profoundly as The Freewheelin' Bob Dylan did for its creator. Before Freewheelin', Dylan was a promising but perhaps derivative young talent. After Freewheelin', he became widely regarded — whether he liked it or not — as the voice of his generation.