'The Freewheelin' Bob Dylan' Ranked 'Best Folk Album of All Time'

On May 27, 1963, Bob Dylan released his second studio album, The Freewheelin' Bob Dylan.

Released just one year after his moderately successful self-titled debut, Freewheelin' was a crucial step forward for the beloved musician as he transitioned from covering traditional folk ballads to composing his own songs, which pushed him even further into the public eye.

The album was promoted with the singles "Blowin' in the Wind" and "Don't Think Twice, It's All Right", which failed to make a dent on the charts. At this point in his career, Dylan was already a legend in the New York folk scene, but he'd failed to translate that popularity into nationwide fame.

Freewheelin' changed everything when it broke into the Billboard Hot 100 at No. 23, introducing a whole new audience to folk music for the first time. It eventually became a best-seller across the country, and is now credited as the first traditional folk album to break into mainstream radio.

Dylan's songs had an unadulterated politicism to them, which led to many fans quickly dubbing him the "Spokesman of a Generation", which Dylan promptly rejected. Tracks like "Masters of War" and "A Hard Rain's A-Gonna Fall" attracted particular attention for their discussion of political injustice, particularly regarding the ongoing civil rights movement in America.

"Blowin' in the Wind" quickly became the album's biggest hit, cementing itself as a generational anthem for the political unrest of the 1960s. Where Dylan's self-titled album had used traditional folk songs to attract a more niche audience, Freewheelin' displayed his own songwriting genius for the first time-and pulled in a much wider listenership as a result. The record even hit No. 1 in the United Kingdom.

Freewheelin' was the beginning of a hugely successful three-album run for Bob Dylan, followed by The Times They Are a-Changin' and Another Side of Bob Dylan, which cemented him as the most successful folk artist of his generation. These records are still credited with making folk popular on a global stage, and Freewheelin' is consistently named the best of the bunch.

In 2025, Illustrate Magazine named The Freewheelin' Bob Dylan as the greatest folk album ever released, with its enduring legacy and timeless lyrics setting the gold standard for the genre.

This story was originally published by Men's Journal on May 27, 2026, where it first appeared in the News section. Add Men's Journal as a Preferred Source by clicking here.

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This story was originally published May 27, 2026 at 6:30 AM.