5 Essential Bob Dylan Albums

A Beginner's Guide to the Work of Bob Dylan

Bob Dylan has been one of the most dynamic artists in the history of modern American music. In over 50 years of the singer-songwriter's career, we have seen a release of over 60 albums including the bootlegs and live recordings.

Some of Dylan's albums are more memorable than others. If you're looking for the best of the best from Dylan, there are just five titles that are absolutely essential. Let's explore these envelope-pushing albums and discover how they affected the turns of American folk-rock.

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The Freewheelin' Bob Dylan (1963)

'The Freewheelin' Bob Dylan' (1963)
'The Freewheelin' Bob Dylan' (1963). © Columbia Records

Bob Dylan's second album, "​The Freewheelin' Bob Dylan" (Columbia, 1963), was one of his most groundbreaking efforts. It can 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. Via songs like "Blowin' In The Wind" and "Bob Dylan's Blues," he showed himself as the groundbreaking singer-songwriter he has since proven to be. Buy from Amazon »

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The Basement Tapes (1975)

Bob Dylan - 'The Basement Tapes' (1975)
Bob Dylan - 'The Basement Tapes' (1975). © Columbia Records

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. Buy from Amazon »

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Highway 61 Revisited (1965)

BoB Dylan - 'Highway 61 Revisited' (1965)
BoB Dylan - 'Highway 61 Revisited' (1965). © Columbia Records

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 and timeless folk-rock classics as "Desolation Row" and "Like A Rolling Stone." This has been considered one of his best albums by everyone from Rolling Stone magazine to Dylan himself. Buy from Amazon »

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Blonde on Blonde (1966)

Bob Dylan - 'Blonde on Blonde' (1966)
Bob Dylan - 'Blonde on Blonde' (1966). © Columbia Records

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 more flow and his synergy with The Band was at its peak. It included such classics as "Sad Eyed Lady of the Lowlands" and "Just Like a Woman." This has consistently been labeled one of the best albums in modern music history.

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Time Out of Mind (1997)

Bob Dylan - 'Time Out of Mind' (1997)
Bob Dylan - 'Time Out of Mind' (1997). © Columbia Records

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 notable albums and made great contributions to the progression of modern music. Somehow, though, this release marked a significant moment in his career. On it, 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. Buy from Amazon »