63. "If You See Her, Say Hello" (1975)
"If You See Her, Say Hello" might be the most painful moment on Blood on the Tracks. Dylan is grappling with fresh grief: "To think of how she left that night," he sings, "it still brings me a chill." The song went through extensive revisions – an early draft's "If you're making love to her, kiss her for the kid" was softened to "If you get close to her, kiss her once for me." But the final version still cuts close to the bone. Hearing Dylan admit "Either I'm too sensitive or else I'm gettin' soft" packs just as much punch as his most venomous songs.