“Trolling” can be the new “pretentious” — a lazy word to instantly dismiss what bugs you without exercising due diligence. Good on Bob Dylan for kicking around long enough to suffer both cheap slams. Thing is, we’ve always liked to think the sly coot is putting us on — lets us pretend he gives a damn what we think. But if Dylan is making any statement with the ten Sinatra-identified numbers on Shadows in the Night (aside from the same one he makes in every interview, that he flat-out loves old songs) it’s one he shouldn’t and doesn’t have to after more than a half-century of recording: The sounds he makes with his mouth are not accidents.
The clinkers here (he has a few) are placed as cannily as Monk’s. That’s an imperfect comparison — Monk could play what he wanted, Dylan’s physical limitations shape his artistic choices no less surely than his melodic or his rhythmic ingenuity. So imagine Monk sometimes favoring the half-dozen, half-dead keys of a battered barroom piano, sometimes trickily playing around them. The performances are more mannered than that image suggests — as with some of the finest of jazz vocalists (would you believe?) the emphasis on nuance here can detract from the story the song has to tell. You don’t hear “Some Enchanted Evening,” you hear Dylan singing “Some Enchanted Evening.”
More often, though, a character emerges, a hopeless romantic in the most literal, pitiful sense of the cliche: too old to love again, too weak to shelve his longing. Dylan sounds 73 going on infinity here, his willed decrepitude deepening the resignation of “Why Try to Change Me Now,” and, more importantly, engulfing “I’m a Fool to Love You” and “Autumn Leaves” in a lonesome pathos, imagining what it must be like to suffer the very last heartbreak of your life. The subtle arrangements — pedal steel throughout, an occasional light horn swell for color — accentuate the bleak mood. But they also smudge the distinctions between pop traditions. At times you wouldn’t even notice that these are songs Bob Dylan isn’t supposed to sing.
Together Through Life and Tempest suggested that Dylan’s turn-of-the-century revitalization was ebbing, and maybe Shadows in the Night is as minor as those predecessors. But that renaissance — Time Out of Mind, “Love and Theft,” Modern Times — couldn’t have happened if Dylan hadn’t re-immersed himself in folk, publicly woodshedding on Good as I Been to You and World Gone Wrong. Maybe these songs will seem a similar jumping off point in retrospect. Or maybe they’ll just stand as another instance of Dylan exercising his genius in the service of democracy, indicating a cultural heritage that’s open to whoever’s willing to claim it with wit and guile.