A Bob Battle: Which of Bob Dylan’s 1960s Albums Is His Best?

Has there ever been a stretch of records as influential and game-changing as Bob Dylan’s output in the 1960s? Dylan continued to push the boundaries of his art while improving dramatically as a songwriter.

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We’ve narrowed the list of his 60s albums to the four we believe are the best. After taking a quick look at each, we’re going to give our verdict on which LP we think was Dylan’s best of the decade.

‘The Times They Are A-Changin” (1964)

Many folks might be surprised to find that The Freewheelin’ Bob Dylan didn’t make this list. In our opinion, The Times They Are A-Changin’ took what was great about that album and advanced upon it. Protest songs like “Ballad Of Hollis Brown”, “Only A Pawn In Their Game”, and “The Lonesome Death Of Hattie Carroll” cut deeper and display more nuance. “Boots Of Spanish Leather” is one of Bob’s best heartbreak songs. And the title track and “When The Ship Comes In” resemble ancient prophecies set to music.

‘Bringing It All Back Home’ (1965)

As if to test the waters, Dylan electrified only the first half of this landmark album. He chose some of his most irreverent material to use for this plugged-in experiment. Songs like “Maggie’s Farm” and “Subterranean Homesick Blues” seemed to be directing all their sass at the staid old world. The second side might have been acoustic in nature. But Dylan still managed to use it to leave behind his folk contemporaries with the hallucinogenic, visionary imagery of songs like “Gates Of Eden”.

‘Highway 61 Revisited’ (1965)

Even as things got a bit more raucous, the electrified songs on this stunning LP gained a bit more musical clarity. As a result, every biting line of the chaotic songs like the title track and “Tombstone Blues” hits hard. But even as the rest of the world was reacting to Dylan’s sea change, he was already moving forward into new avenues. This album features delicate mid-tempo tracks like “Queen Jane Approximately” and “Just Like Tom Thumb’s Blues”. And we still haven’t even mentioned the epics “Ballad Of A Thin Man” and “Desolation Row”.

‘Blonde On Blonde’ (1966)

After Blonde On Blonde, Dylan walked away from the limelight for a while. Perhaps he did it because he left it all on the table with this incredible double album. Some of the old mayhem was still present, most notably on the album-opening “Rainy Day Women #12 & 35”. But an elegant sadness prevails for much of the record, as Dylan surveys a series of failed relationships. At least until he takes an entire side to sing the praises of his wife on the epic “Sad Eyed Lady Of The Lowlands”.

The Decision

All four of these albums represent absolute milestones in music history. In other words, it’s not an easy choice to select just one. We’re going to throw out Bringing It All Back Home, if only because the first side features a few somewhat forgettable comic numbers.

Bringing It All Back Home and The Times They Are A-Changin’ are pristine. But Blonde On Blonde is equally spotless, and it raises the ante with two LPs of material. Thereby, it wins by a nose in this colossal battle.

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