‘Why Bob Dylan Matters’ Playlist

‘Why Bob Dylan Matters’ Playlist

“Blowin’ in the Wind”

Three verses, each with three questions, each question extending over two lines, and each followed by the same enigmatic answering couplet: “The answer, my friend, is blowin’ in the wind / The answer is blowin’ in the wind.” The artistic structure and perfection of this song, not just its powerful message, is what keeps it around, and what I talk about in the book.

“Boots of Spanish Leather”

Inspired by the absence—in Italy, not Spain—of Dylan’s girlfriend Suze Rotolo. This beautiful song belongs to a duet tradition that goes way back, through Shakespeare to the ancient poets, with the singer trying to get his love to come back across the lonesome ocean. One of the many classic songs Dylan sang for the last time in Rome in November, 2013.

“Chimes of Freedom”

Parts of this song Dylan learned from folksinger Dave Van Ronk, who remembered the chorus of a sentimental late nineteenth-century song, “Chimes of Trinity,” about Trinity Church in lower Manhattan, a song that Van Ronk’s grandmother sang to him. As I argue, Dylan adds to this ingredient his adaptation of a poem of Arthur Rimbaud, the volatile and precocious young French Symbolist poet, with whose surrealistic lyrics Dylan was forming a bond in 1963 and 1964.

“When I Paint My Masterpiece”

Opener during the Rolling Thunder Revue tour (1975–76), by which time Dylan had indeed “painted” his new masterpiece, Blood on the Tracks. From 1971, the song is one of a number that find Dylan thinking about the Eternal City, the “streets of Rome” with which this song begins, connecting back to an earlier unrecorded song, “Goin’ Back to Rome,” that Dylan sang in Greenwich Village in early 1963, including the couplet “I’m going back to Rome / That’s where I was born.”

“Tangled Up in Blue”

The great song from Blood on the Tracks went through much revision to reach the two final recorded versions, as a small notebook in the new Tulsa archives, with unrecognizable earlier drafts, clearly shows. I include some of those earlier drafts in my discussion of this, the only survivor of the 1970s in Dylan’s recent setlists, at one point entitled “Dusty Sweatbox Blues,” then “Blue Carnation,” and finally—just right—“Tangled Up in Blue.” In 2017 in performance Dylan gave the song a new arrangement which has utterly transformed it.

“If You See Her, Say Hello”

Beautiful song, whose different versions, both recorded and in performance, show how the end of a relationship can come across in different ways—tender and regretful, hostile and savage, amusing and absurdist—depending on lyric and vocal changes.

“Changing of the Guards”

A song that looks back across the sixteen years to when it all began, as well as to what was about to happen, when your hearts “must have the courage for the changing of the guards,” anticipating the born-again phase that was already in progress in 1978.

“Tryin’ to Get to Heaven”

Here, Dylan stitches together lines and verses from the songs in his blues, gospel and folk traditions. Drawn from folks like Woody Guthrie to Tom Rush to the anthologies of Alan Lomax, Dylan produces an exquisite song, the story of someone in trouble, on the run, looking for one last shot at redemption, heading down the river, “tryin’ to get to heaven before they close the door.”


The first five lines of this song come from Robert Burns’ 18th century poem/song, “My Heart’s in the Highlands.” The rest is from the imagination of Bob Dylan, which includes updating the romantic encounter captured in the 1975 classic, “Tangled Up in Blue,” a song whose world the singer in 1997 tries in vain to resurrect, only to be told he “picked the wrong time to come.”

“Workingman’s Blues #2″

Another beautiful song showcasing the new intertextual (“stealing”) compositional methods of the last twenty years. This song invokes, alters and repurposes some verses of Confederate poet Henry Timrod, and Ovid, Roman poet, in exile from 2000 years ago. The song is blending these disparate texts and creating a story that exists throughout time. Dylan makes these sources his own in a manner not different from similarly intertextual poets like T. S. Eliot, and Ovid himself.

“Early Roman Kings”

Dylan is at his literary and musical best in this song, which has been a favorite in recent performance. Its menacing words underscored in the fantastic accompaniment of his band. The song touches on the Roman Kings, a 1960s New York gang, who were then the actual kings of ancient Rome. The singer morphs into Odysseus, taunting the Cyclops from Homer’s Odyssey, and Motown seems to be in there too. This mix is typical of the deliberate incongruities that have always been part of the artistry of Bob Dylan.


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