How is someone like Bob Dylan going to write a book that purports to explore The Philosophy of Modern Song? Such a title seems to suggest an academic approach to analyzing songwriting. Dylan may be clever, but he's no academic. It implies a study performed with discipline. As anyone who ever read his rambling autobiography Chronicles: Volume One or the liner notes of Highway 61 Revisited knows, Dylan sneers at discipline.
So what the hell is this book? Well, it is neither academic nor disciplined, but it is very, very Dylan. It's a look at a selection of 66 songs through a lens that sometimes squints and rolls and often widens with awe.
What kinds of songs would Dylan choose to examine? Square pop standards, rock and soul classics, and country relics. He likes the kinds of lyrics you'd think Dylan would like. He likes songs about cowboys and outlaws, wronged men and untrustworthy women (he takes no measures to slap masks on his well-documented misogyny, at least none that are actually effective), nomads, god-fearers, and clowns who think they're hip but are actually full of hot air.
While he doesn't follow any established rules of analysis, he does establish his own structure. First he places you in the song with a second-person tale not too different from those text stories kids always skipped over when reading EC comics, but Dylan's dogs are shaggier than any beastie Al Feldstein ever imagined. Dylan might cast you as the clueless, self-impressed misanthrope of "My Generation", or he might rewrite your role from the generic barfly of Webb Pierce's "There Stands a Glass" to a monstrous participant in the Mai Lai Massacre for some reason. Hey, man--he's just riffing.
Next up, Dylan gives something resembling a more formal analysis of the song. There's a good deal of historical information in a lot of these, though since he's already established himself as an unreliable narrator (with and prior to this book), you should probably do some cross referencing before taking too much of it as fact (I'm sure never going to trust anyone who'd say something as misguided as "the laws of God override the laws of man every time," which would be less off-putting in a world where people weren't constantly citing illogical laws of gods they invented to justify oppressing others). Or you may just want to throw up your hands or scratch your head trying to figure out how that horrific fiction that accompanies "There Stands a Glass" sets up an "analysis" that's actually a canned biography of the guy who invented the Nudie suit.
If you wandered into a Dylan book and expected anything but a lot of head scratching and hand throwing, you probably haven't been following this guy's career very closely. Any college prof who assigns The Philosophy of Modern Song to students taking a course with a title like The Philosophy of Modern Song sure hasn't been. Those who'll most dig it are fans who delight in Dylan's penchant for confounding, his venomous humor, his intermittent insightfulness, and his often partially concealed humanity that makes a fair share of this book palatable. A fair share is pretty insufferable too.