Essential Bob Dylan Albums

Bob Dylan's second album, The Freewheelin' Bob Dylan (Columbia, 1963), was one of his most groundbreaking efforts. It could be held responsible for putting Dylan on the map in the first place. On Freewheelin', Dylan seemed to have catapulted past the Woody Guthrie-lite of his Columbia debut, and shone himself as the groundbreaking singer-songwriter he has since proven to be.

Easily one of Dylan's most influential recordings, The Basement Tapes was one of rock and roll's original indie albums. The story of this record began with Dylan's motorcycle crash in 1966. During the year following the accident, he and the Hawks (aka the Band) started working in a homemade studio in the basement of the house known as Big Pink. After a number of remixes and overdubs, Columbia released The Basement Tapes almost a decade after the tracks were laid down. Of the 24 tunes on the final collection, eight weren't recorded in the basement. Not that this small fact inhibited the reach of the album, as so many big-time rock and contemporary folk-rock artists cite this record as a major influence.

Although some of Bob Dylan's previous records had included some more rock-infused tracks, his sixth studio album, Highway 61 Revisited, was the first to be entirely considered a rock album. It included such extraordinary, timeless folk-rock classics as "Desolation Row" (purchase/download) and "Like A Rolling Stone" (purchase/download), and has been considered one of his best albums by everyone from Rolling Stone magazine to Dylan himself.

Where Highway 61 firmly established Dylan as a trendsetter and path-forger in the new folk-rock sound, Blonde on Blonde was a much more decisive record in terms of Dylan's own relationship with the new sound. His loquacious, imagery-laden poetry had become more flowy, and his synergy with the Band was at its peak. It included such classics as "Sad Eyed Lady of the Lowlands" (purchase/download) and "Just Like a Woman" (purchase/download), and has consistently been labeled one of the best albums in modern music history.

This 1997 release—his 41st album—saw Bob Dylan teaming up with the great producer and multi-instrumentalist Daniel Lanois. Between The Basement Tapes and Time Out of Mind, Dylan certainly recorded some hugely notable albums, and made great contributions to the progression of modern music. Somehow, though, this release marked a significant moment in his career where he was finally able to find common ground between the roots-blues-rock sound he'd pioneered and the folk singer-songwriter vibe that had propelled him to fame in the first place. The album was a little darker and more mysterious, but the musicality is undeniable.