Bob Dylan Reveals Himself Through 66 Songs

And it’s the closest we’re probably going to get.

a photo of bob dylan with musical notation overlaid
Erik Carter / The Atlantic; Getty

As an author of all kinds of work—songs, poetry, a memoir, radio-show commentary, the occasional film script or Nobel lecture—Bob Dylan has been engaged for more than 60 years in an inquiry into authorship itself. From his earliest days as a folk singer in MacDougal Street coffeehouses, he has been known for drawing freely, often brazenly, from the work of his predecessors (and occasionally his contemporaries), employing the “folk process”—through which each singer makes additions or alterations to a shared body of material—to produce work idiosyncratically his own. In Chronicles: Volume One, his 2004 book of impressionistic reminiscences, Dylan seems to have mined an old issue of Time magazine and an assortment of other sources to construct a collage representing his memories and ideas. Even with his paintings, many of which appear to be based on still frames from movies and published photographs, Dylan has tempted accusations of appropriation. His whole body of work is largely concerned with the question, “Who really made this?”

The answer to that may be “Who cares?” And the answer to that is: Bob Dylan cares. The nature, the mechanics, and the meaning of creativity, especially as it pertains to music, matter a lot to him, as he makes abundantly clear with his new book, The Philosophy of Modern Song. A collection of short essays, lyrical riffs, chunks of facts, and unpredictable digressions, generously illustrated with historical photos suitable for enjoyment at the coffee table, the book presents Dylan’s thoughts on a quirky selection of 66 songs recorded over the past 100 years or so.

The book is all about authorship—how singers remake songs through their performances, how listeners re-create them in their minds to suit their needs, and how Dylan can make songs of every type his own by the way he thinks and writes about them. It’s a work of authorship, obviously, and at the same time a critique of, and a bit of a prank on, the idea of authorship, too.

Much of Dylan’s philosophy on the workings of popular music since the rise of recordings is centered on performance rather than composition. “Perry Como lived in every moment of every song he sang,” Dylan writes in a chapter on “Without a Song,” the valentine to singing that Frank Sinatra recorded with Tommy Dorsey and His Orchestra in the 1940s, and that Sinatra’s acolyte Como made a smooth-music hit in the early ’50s. Como, Dylan explains, “didn’t have to write the song to do it … When he stood and sang, he owned the song and he shared it and we believed every single word.”

Dylan demonstrates here how a skilled vocalist such as Como could, through a sensitive interpretation, be as creatively expressive as a songwriter. If the point seems incongruous coming from a songwriter of genius, it befits a writing singer who, late in life, made five albums’ worth of material originally recorded by singers such as Sinatra and Como.

Dylan hangs each chapter on a particular recording of a song (“Whiffenpoof Song,” released as a single by Bing Crosby in 1947; “On the Street Where You Live,” released as a single by Vic Damone in 1956), and generally focuses on the performer or performers, though exceptions to this abound. Dylan begins some chapters with a looping, free-form narrative, spinning an imaginative tale connected in some way to the idea or theme of the song. For Ray Charles’s recording of “I Got a Woman,” for instance, we get a punchy little noir story about a tired guy driving across town to certain disappointment, “sweat-soaked shirt sticking to his car seat,” tapping “the steering wheel in time to Fathead Newman’s tenor saxophone.”

These sections are certainly the most overtly literary parts of The Philosophy of Modern Song, and the literature they conjure is the racy pulp of bus-depot book racks in mid-century America: the fiction of writers like James M. Cain and Jim Thompson, who luxuriated in taboo and whose work, by the early 1960s, came to be seen by the culture as the lingua franca of cool. Dylan revels in this world of “gypsies, tramps, and thieves” in a way that feels daring in a quaint, almost corny way, but he also seems sometimes strangely desperate to shock. For the chapter on Webb Pierce’s cover of “There Stands the Glass,” for example, Dylan goes far in making the song his own, spinning a weird fictive backstory about a combat vet haunted by images of the atrocities he committed in the name of duty: “He sees a little boy two years old and he murders him, he sees his buddies slit a little girl open with a knife, strip off her clothes and rape her, then he shoots her with an automatic, his horny buddy.” Told with unshakable specificity, the story doesn’t have a thing to do with the song, but it shocks like the high-voltage fiction of the trash literati.

In many of the chapters, Dylan treats the authors of the songs like poster boys out of a fanzine, providing tidbit-rich arcana such as the fact that Ricky Nelson, whose rockabilly ballad “Poor Little Fool” made No. 1 on the very first Billboard Hot 100 chart in 1958, was not only a skilled tennis player and trapeze artist, but a starting player on his high-school football team, following the cleated footsteps of his father, Ozzie Nelson, who had once been starting quarterback on the Rutgers University team. In other cases, Dylan withholds biography in service to the work. “Knowing a singer’s life story doesn’t particularly help your understanding of a song,” he writes in the chapter on “Pump It Up,” by Elvis Costello. “It’s what a song makes you feel about your own life that’s important.” Popular music is a collaborative art, Dylan reminds us, with not only writers, performers, musicians, and record producers playing parts, but the audience also contributing through the points of reference each listener brings to the music. In a sense, Dylan seems to suggest, a song’s listeners are its authors too.

At the same time, for Dylan to stress the irrelevance of biography is to remind us of his own biography and its role in his work. His resistance to personal scrutiny and skill at obfuscation and self-invention are not distractions from the story of his life; they are the story of his life. Chronicles: Volume One reads as a vividly accurate account of the mind of a brilliant fabulist, a master of entwined fact and fiction. If he never gets around to writing Volume Two, Dylan has provided a semblance of a sequel to Chronicles in The Philosophy of Modern Song. Though the book is ostensibly about songs by other artists, there is the outline of another book, a shadow book about Dylan, within it.

We can see a few things clearly. From the selection of songs and singers, one could conclude that Dylan has little interest in women as creative artists. A mere four of the dozens of artists featured in the book are female (five if you count The Platters, who had one female singer), and the women who collaborated with men in the songwriting—or, in some cases, wrote the songs on their own—are mostly ignored or glossed over. When he does discuss women, Dylan often depicts them as dark temptresses and shrews, luring men to their doom: witchy women, black-magic women. Of course, he’s correctly reflecting the way women are depicted in the songs. But he’s the person who chose the songs. And just think of the countless artists not included: Loretta Lynn, Joni Mitchell, Laura Nyro, Dolly Parton, Pink, Solange, Taylor Swift. I promised myself not to get caught up in second-guessing every song choice Dylan made, because any person’s selection of 66 songs, including my own, would inevitably have innumerable holes and omissions. Still, Dylan’s refusal to acknowledge the depth of women’s contributions to American song is indefensible.

We see, too, that Dylan thinks very little of hip-hop—or, more likely, that he doesn’t think about it at all. We see that he has some discomforting ideas about marriage, including the thought that polygamy would solve a lot of marital problems. “It’s nobody’s business how many wives a man has,” he says. I guess we can—or should—assume he’s joking.

We also find a few intriguing surprises: That Dylan knows much more than I ever realized about a range of obscure subjects, such as the convoluted authorship of Sinatra’s “Strangers in the Night”; the production history of the Disney documentary White Wilderness; and the intricacies of translating Albert Camus from the French. In the absence of endnotes, there’s no knowing the source of such material. We can only take what pleasure there is in it and marvel at the author’s unfading ability to test the meaning of authorship and make the work his own.