“The Philosophy of Modern Song,� the title of Bob Dylan’s new book, may sound like a tendentious academic tract or undercooked master’s thesis, but it’s neither. Imagine sitting across from Bob Dylan in a quiet corner of a smoky bar, knocking back shots and gradually getting looped as he rambles on about the songs he’s loved, been inspired by, stole from, or just awed by the craftsmanship and passion. A few hours would probably teach you more than you’d learn in a couple of years in a typical classroom. Here’s Bob, pausing in his eulogy for Warren Zevon and rhapsodizing about the song “Dirty Life and Times� on “The Wind�—the album Zevon recorded as he was dying of cancer—to pay homage to Ry Cooder’s subtle and heartbreaking accompaniment: That’s Ry Cooder playing here, and Ry Cooder is a man with a mission. There was no road map when he was trying to figure out the connection between Blind Lemon Jefferson and Blind Alfred Reed, the place where conjunto met the gutbucket blues, where even a jake-leg could do a cakewalk. One of the cool things about being Bob Dylan is that you don’t have to give a damn what anybody thinks of your musical taste or your literary style. You’ve got nothing left to prove; you already proved it nearly 60 years ago before you’d even hit 30 back when the grandparents of today’s social-media “influencers� might have heard “the voice of a generation� the first time around. Jimi Hendrix may have covered you back in the day, but now you can wax eloquent about Vic Damone, Frank Sinatra, Rosemary Clooney, and Dean Martin, and who would dare argue? About Perry Como, Dylan writes: [He] lived in every moment of every song he sang. He didn’t have to write the song to do it. He may have believed the songs more than some of the people that wrote them. When he stood and sang, he owned the song and he shared it and we believed every single word. Exhuming the 1947 Bing Crosby recording of “The Whiffenpoof Song,� he declares: This song is the grinning skull. An in-crowd song, a song with a pedigree, a song in the Social Register. Not meant for the middle class to understand—seems to house a deep dark secret…It paraphrases Kipling and lists a couple of songs no one’s ever heard. A lot of bones and skeletons in this song. Even the word ‘Whiffenpoof’ is a word to dispel spirits, and the melody is ancient—the last gasp, the beginning of the end. Some years ago I picked up a double CD anthology titled “John Lennon’s Jukebox,� containing songs that Lennon had collected and stocked in a KB Discomatic portable jukebox. Apart from a lot of both classic and obscure pop recordings, its main appeal is not as just another oldies collection, but as a glimpse into the psyche and emotional inner life of one of the leading popular songwriters of the 20th century. And that’s exactly what’s at work here in Dylan’s “Modern Philosophy� book, along with an engaging freewheeling narrative lacking in the Lennon compilation. It’s a fast read; some of the pieces are as short as two or three pages, and none run more than seven or eight pages, including evocative pictures befitting a coffee-table book like this. I made myself a streaming playlist of the 66 selections Dylan writes about, and most of the essays can be read in the time it takes to listen to the accompanying song. One of the most appealing aspects of the book is the way a favorite song will send Dylan off on a reverie of free association that can meander in ever-widening circles until, before you know it, you’re right back at the center again. Writing about the Drifters’ “Saturday Night At the Movies� (a minor follow-up that recycled the melody from their better-known “Under the Boardwalk�), Dylan addresses not the group or the song, but the subject matter, American movies and moviegoing. Along the way, he name-checks the anti-heroes of such classic American films as Cool Hand Luke, Butch Cassidy and the Sundance Kid, Dirty Harry, Super Fly, Taxi Driver, Little Caesar, The Public Enemy, The Wild One, Rebel Without a Cause, Ace In the Hole, On the Waterfront, High Noon, The Treasure of the Sierra Madre, and 12 Angry Men. “America has always been a great melting pot but there are a few things that have been created here and then given back to the world,� he writes. “It may be fun to drive a Ferrari, but Detroit will always be the automobile’s home. Admire the French violinist Stéphane Grappelli, but King Oliver, Buddy Bolden and Louis Armstrong will remain the beating heart of jazz. Fellini, Kurosawa, and other foreign directors may be great, “but we all know where the film industry got its first slap on the ass and drew its initial breath.� Many of us already knew of Dylan’s admiration for singer-songwriters like Pete Seeger, Johnny Cash, and Waylon Jennings. But here’s Dylan commenting on a truly deep track, a cover version of Stephen Foster’s “Nelly Was A Lady,� one of the 19th-century popular composer’s lesser-known tunes, from the 2004 tribute anthology,“Beautiful Dreamer�: Stephen Foster is the counterpart to Edgar Allan Poe. This is one sweeping song that is designed to make anybody who’s ever lived a life just lie down and weep. A lot of sad songs have been written but none sadder than this. Both the lyrics and the melody. Alvin Youngblood Hart’s is as good a version as you’ll ever hear…The guitar turnarounds are a slow cakewalk between heartbroken verses, loss shared on the front porch. The tune will stay in your head long after you have forgotten the story and every time you hum it a tear will roll down your cheek. My father adored Stephen Foster and introduced me to his music. I would have loved to hear what he thought of this version which is, as Dylan said, a real heartbreaker. When I inherited Dad’s CD collection after he died in 2009, I found the copy of this Foster anthology that I’d gifted him with several years earlier, still unopened. But that’s OK. I’ll never know what Dad would’ve thought of it, but like so many other songs I know he loved, it carries special meaning for me, and Dylan explains why. Music, he concludes, “is of a time but also timeless; a thing with which to make memories and the memory itself….Music transcends time by living within it, just as reincarnation allows us to transcend life by living it again and again.�