Bob Dylan’s 20 Best Songs

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Top Songs is a feature in which we definitively handpick the very best songs in an artist or band’s catalog. Sounds simple, right? Oh, if only.

A short while ago, this would have been just another dumb ranking of songs. However, if you abide by the recent opinions of the Swedish Academy, Bob Dylan songs now rank as literature — poetry, to be precise. I’ve always loosely defined a poet as someone who sees the same things as the rest of us through eyes capable of detecting some hidden truth and then possesses the voice to speak that truth. It’s what Dylan sings of in “A Hard Rain’s a-Gonna Fall” — that concept of the artist as messenger: “reflect it from the mountain so all souls can see it.” So, I thought it fitting when Patti Smith performed the song at the Nobel ceremonies, not so much because the composition, to the layman, builds and bursts with imagery and feels like we think poetry ought to, but because it, more than a half-century ago, charged songwriters with the same artistic obligations as poets, painters, and novelists. I do believe the Swedish Academy deserves praise for acknowledging Dylan’s contributions to literature, but let’s not pretend that they’ve told us anything we didn’t already know for decades about Bob Dylan or the power of popular music.

As for this list, picking among Dylan’s vast body of work wasn’t as difficult as anticipated. One might beg an editor for five more songs, but that only begets another five and so on. Suffice it to say, every song here touches a nerve, scrapes away at some truth, or puts into words and arrangements something we might not otherwise be able to tap into on our own. From the beginning, Dylan’s drawn from tradition, old songs, and literature, sifting through other accounts and reconciling it with the world around him. In many ways, he is that poet, interpreting humanity and reflecting it back to us in all its beauty, ugliness, and cruelty. If strangers in the distant future want to learn about us, the real story, they could do far worse than picking up a few Dylan records. In the meantime, here are 20 Bob Dylan songs that only he — poet, songwriter, or trapeze artist — could have reflected from the mountain.

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