Bob Dylan/Tear Jerker

This legendary folk musician has a lot of very emotional songs.

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• Some of the songs on The Times They Are a-Changin', especially "The Ballad of Hollis Brown", when you consider that that kind of thing can often happen in real life, to say nothing of the real-life tragedies which inspired "The Lonesome Death of Hattie Carroll", "Only a Pawn in Their Game", and the unreleased "Death of Emmett Till."
• The best example is probably just about every song on Blood on the Tracks, which was written shortly before (not after) his divorce. It is commonly considered to be a defining example of break-up music.
  • "Sara" is, on its own, a well-written and melancholic love song. But realizing that it was one of the few songs that Bob Dylan wrote about his personal life—in an attempt to salvage his failing marriage—makes the emotion within it a lot more powerful. And then, you find out that it didn't work.
• "Sweetheart Like You," because of the implication that due to Humans Are the Real Monsters and Crapsack World, the genuinely good woman he's singing to won't be able to make it in the world.
• It can be hard to get through a listen of "Ballad in Plain D" without completely falling apart. Dylan reflects on a failed relationship, comes to terms with the pain he's caused and the mistakes he's made, then caps it off with a gut-wrenching harmonica solo...
• "Goin' to Acapulco", especially in I'm Not There.
• Also: "Forever Young", "Knocking on Heaven's Door", "It's All Over Now, Baby Blue", and "Sad-Eyed Lady of the Lowlands".