Bob Dylan’s Infinite Playlist

Inside his new book The Philosophy of Modern Song

Young Bob (Image: Simon and Schuster)

I know, I know. That title. I was half-expecting some sort of dense, academic, pedagogic treatise as Dylanesquely incomprehensible (or should that be incomprehensibly Dylanesque?) as the lyrics to “Gates of Eden.”

But I’m here to say, loud and proud: I love, love, love this book, and I bet you will, too. I need volume two yesterday. And volume three after that.

What Dylan does here is provide his own take on 66 songs from as far back as 1849 (Stephen Foster’s “Nelly Was A Lady”) and as recent as 2003 (Warren Zevon’s “Dirty Life and Times”). The 1950s get the most attention (28 songs) followed by the 1970s (14 songs) and the 1960s (13 songs). A half dozen tunes from 1980 and later are examined, while five more fall into the pre-1950 category.

Many of the essays begin in similar style:

“In this song you’re hemmed in, going round and round the loop, doing full turns…” (Mose Allison’s “Everybody Cryin’ Mercy”).

“In this song the protagonist has proven his worth, he’s accounted for himself in all good ways…” (Harold Melvin & the Blue Notes’ “If You Don’t Know Me By Now”).

“In this song, you’re feeling as good as can be, and don’t need to be convinced.” (Sonny Burgess’ “Feel So Good”).

“In this song you’ve been saving your pesos, penny-pinching all your small change.” (Roy Orbison’s “Blue Bayou”).

“In this song everything goes off track.” (The Temptations’ “Ball of Confusion”).

Dylan provides a page or two about what the song is saying, a generally literal reading of the lyrics. Then there’s a second part to the essay, a page or two about how the song can be taken, where it fits and what it means in larger cultural and historical context, and why it works for that particular singer at that particular time in music, and maybe even some of the influences that helped shaped the song, or that the song helped shape subsequently.

Bob Dylan The Philosophy of Modern Song, Simon and Schuster 2022

The overall effect is like sitting in a room with Bob himself, putting a Spotify playlist on shuffle (yes, there are already Spotify playlists with all these songs on them; this is the best one I’ve found), and hearing one of the greatest songwriters of all time hold court in a grand and glorious stream of consciousness that takes flight from whatever aspect of the song tickles his brain. Only occasionally are the insights not particularly insightful (it’s pretty obvious that “The Pretender” is “arguably one of Jackson Browne’s greatest songs”). Most often, though, they’ll have you thinking about the song in a new and different way.

Take Dylan’s essay on The Who’s “My Generation,” for example. In the first part, he notes that “this is a song that does no favors for anyone, and casts doubt on everything.” He goes on to note how the singer is “in an exclusive club … you can’t conceal your conceit, and you’re snobbish and snooty about it … You’re looking down your nose at society and you have no use for it. You’re hoping to croak before senility sets in.”

Which all kind of fits in with how most people hear the song. Then, in the next paragraph: “In reality, you’re an eighty-year-old man, being wheeled around in a home for the elderly, and the nurses are getting on your nerves. You say why don’t you all just fade away.” There’s a new way of looking at the Who’s anthem!

In the second part of the essay, Dylan ruminates on the notion of what, exactly, a generation is, and how “every generation gets to pick and choose what they want from the generations that came before with the same arrogance and ego-driven self-importance that the previous generations had when they picked the bones of the ones before them.” Then, in the midst of name-checking Gloria Swanson, Marlon Brando, Elvis Presley, Little Richard, Nazis and Nora Desmond, he ties it all back to Pete Townshend – in less than two pages.

Dylan writes about “the song of the gambler” (Elvis Presley’s “Viva Las Vegas”), “the song of seduction” (Rosemary Clooney’s “Come On-A My House”), the “song of a traveling bandit” (Willie Nelson’s “On the Road Again”), “the song of the con artist” (Hank Williams’ “Your Cheatin’ Heart”), the song of the sufferer (John Trudell’s “Doesn’t Hurt Anymore”) and the “ballad of the tortured soul (Marty Robbins’ “El Paso”). He writes about The Fugs and The Clash, Vic Damone and Dean Martin, Santana and The Eagles, Johnny Cash and Uncle Dave Macon, Rosemary Clooney and Judy Garland.

The Philosophy of Modern Song back cover image (Image: Simon and Schuster)

There’s a lot of territory covered here – and it’s all gloriously tied together with photos and images that go far beyond the conventional, providing laughter and creating new associations and connections with almost every turn of the page. Carmen Miranda for Little Richard’s “Tutti Frutti”? Of course! A sultry pulp babe from the cover of Best Detective for Ray Charles’ “I Got A Woman”? Excellent! And for the 1956 Osbourne Brothers’ track “Ruby, Are You Mad?” we get the iconic image of Jack Ruby shooting Lee Harvey Oswald seven years later, plus Ruby’s mugshot. Wow.

Plus all those photos of old record stores – they make you want to crawl into the image and start sorting through the stacks. They’re a vivid reminder of how deeply important music is to so many people – and how important these songs are to Dylan.

So grab this book. Pick a song and turn to its essay. Play the tune as you allow Dylan to hold the prism of that unique composition up to his own light, revealing vibrant colors you’ve never heard before.

No, seriously Zimmy – I need volume two.



Craig Peters
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Craig Peters

Craig Peters has been writing about music, pro wrestling, pop culture and lots of other things since the Jimmy Carter administration. He shook Bruce Springsteen’s hand in 2013, once had Belinda Carlisle record the outgoing message on his answering machine, and wishes he hadn’t been so ignorant about the blues when he interviewed Stevie Ray Vaughan in 1983.

One thought on “Bob Dylan’s Infinite Playlist

  • November 26, 2022 at 11:42 am

    Great review.
    I was hoping for some John Prine (“Pure Proustian existentialism…. Midwestern mind trips to the nth degree.” – Bobby Z.) or Leonard Cohen (“When people talk about Leonard, they fail to mention his melodies, which to me, along with his lyrics, are his greatest genius…. Even the counterpoint lines—they give a celestial character and melodic lift to every one of his songs. As far as I know, no one else comes close to this in modern music.” – B.Z.),
    But… Volume II!


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