History TearJerker / TomWaits

** On a similiar topic (though with a very different sound) is "Day After Tomorrow" from ''Music/RealGone'', an excellent and extremely sad ballad about a soldier who hates the war is finally coming back home. It helps that it was written as a protest song of the Iraq war.

* His original version of "[[https://www.youtube.com/watch?v=PHyvjdn4rFk Downtown Train]]" from ''Music/RainDogs'' is a bit sad, but [[https://www.youtube.com/watch?v=KJWNcXV884I Everything But The Girls' version'']] is heartbreaking.

--> ''She was fifteen years old and had never seen the ocean, and the climbed into a van with a vagabond. [[FridgeHorror The last thing she said]] was:" I love you, mom". [[TitleDrop And a little rain never hurt no one]].''

* "[[http://www.youtube.com/watch?v=0jyVZNrWkow If I Have To Go]]" from "Orphans, Bawlers, Brawlers and Bastards" has made multiple grown men sniffle and cry.

* "[[http://www.youtube.com/watch?v=ea8qsGDNZ6Q Never Let Go]]" from "Orphans, Bawlers, Brawlers and Bastards" is another one.

** "Children's Story" from "Orphans: Brawlers, Bawlers & Bastards" is a particularly bad one -- and he doesn't even sing. It is also very, very depressing. Even worse if it's [[http://www.youtube.com/watch?v=aYVlHqCC4Qo animated...]]

* "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: [[spoiler: 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.''
* "[[http://www.youtube.com/watch?v=0jyVZNrWkow If I Have To Go]]" has made multiple grown men sniffle and cry.
* His original version of "[[http://www.youtube.com/watch?v=PHyvjdn4rFk Downtown Train]]" is a bit sad, but [[http://www.youtube.com/watch?v=KJWNcXV884I Everything But The Girls' version'']] is heartbreaking.
* "[[http://www.youtube.com/watch?v=ea8qsGDNZ6Q Never Let Go]]" is another one.
* "[[http://www.youtube.com/watch?v=2oGVDLcpXQ8 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 [[http://www.youtube.com/watch?v=aYVlHqCC4Qo animated...]]
* Everything on ''Alice'' that isn't NightmareFuel is this. Either that, or it's Table Top Joe.

* And from the new album, "Pay Me".
** And "Back in the Crowd," a heartbreaking plea for an ex-lover to go back to seeing him as just another stranger rather than condemning him to the melancholy yearning of being JustFriends when they've been so much more to one another.
* "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 [[http://www.youtube.com/watch?v=gOiAQtLBJLA&feature=relmfu live versions]] that morph into "Summertime" by the end.

* "Come On Up To The House", which almost perfectly describes the feeling of depression.
* "Hell Broke Luce" is one when you realise that it's based on the story of a real soldier, Jeff Lucey, who killed himself after returning home from going to war.
* As abstract as its lyrics may be, "Time" has an irrepressible melancholy to it that's impossible to shake. The final verse takes the cake, though.

* ''She was fifteen years old and had never seen the ocean, and the climbed into a van with a vagabond. [[FridgeHorror The last thing she said]] was I love you mom. [[TitleDrop And a little rain never hurt no one]].''

* 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.

-->''"Well, things are pretty lousy for a calendar girl, the boys just dive right off their cars and smash into the street,"'\\

''Just like a stranger, with the weeds in your heart, and pay the fiddler off 'til I come back again."''

-->''"Well, things are pretty lousy for a calendar girl, the boys just dive right off their cars and smash into the street,"''\\

* "Hell Broke Luce" is one when you realise that it's based on the story of a real soldier, Jeff Luce, who killed himself after returning home from going to war.

* His original version of "[[Downtown Train http://www.youtube.com/watch?v=PHyvjdn4rFk]]" is a bit sad, but [[http://www.youtube.com/watch?v=KJWNcXV884I Everything But The Girls' version'' is heartbreaking.

About half of [[Music/TomWaits this innovative musician's output]] (when he isn't being [[NightmareFuel seriously scary]]) [[TearJerker can fall under this category]].

About half of [[Music/TomWaits this innovative musician's output]] (when he isn't being [[NightmareFuelUnleaded seriously scary]]) [[TearJerker can fall under this category]].

* Everything on ''Alice'' that isn't HighOctaneNightmareFuel is this. Either that, or it's Table Top Joe.