Tom Waits/Tear Jerker

About half of this innovative musician's output (when he isn't being seriously scary) can fall under this category.

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• "Christmas Card From a Hooker in Minneapolis" and "Georgia Lee". The album Blood Money (originally the score of a rock opera he co-wrote) contains a few pearls of melancholy, such as "Lullaby" and "The Part You Throw Away".
• "Martha" is especially impressive when you listen to it and realize he wrote it at the age of 21!
• The Black Rider has its moments, but the strangest one is "Lucky Day." It seems like a little ranted remembrance of a man's life. It's not to sad on its own, just melancholy and even funny at times. Then you see the play and you find out its context: the character singing it has just gone stark raving mad after accidentally murdering his bride-to-be on their wedding day, and he's being led off to hell by Pegleg the Devil. That's soul crushing.
• "If I Have To Go" has made multiple grown men sniffle and cry.
• His original version of "Downtown Train" is a bit sad, but the 'Everything But The Girls' version is heartbreaking.
• "Never Let Go" is another one.
• "Take It With Me" can always open the ocular floodgates.
  • "Children's Story" is a particularly bad one -- and he doesn't even sing. It is also very, very depressing. Even worse if it's animated...
• Everything on Alice that isn't Nightmare Fuel is this. Either that, or it's Table Top Joe.
• That goes double for Bone Machine. "I Don't Wanna Grow Up" is a particularly poignant example, and "Dirt In The Ground" is just melancholy as all hell.
• And from the new album, "Pay Me".
• "Ruby's Arms," "No One Knows I'm Gone," "Lucky Day," "Flower's Grave..." The list goes on. Tom Waits' ballads will destroy your soul.
• "San Diego Serenade"... Just... Just "San Diego Serenade".
• "Burma Shave". Especially the long, improvised live versions that morph into "Summertime" by the end.

...so hush now, baby, dooooon't you cry, don't you cry, don't you cry...