- "Christmas Card From a Hooker in Minneapolis" from Blue Valentine and "Georgia Lee" from Mule Variations. 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" from Closing Time 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" from Orphans: Brawlers, Bawlers & Bastards has made multiple grown men sniffle and cry.
- His original version of "Downtown Train" from Rain Dogs is a bit sad, but Everything But The Girls' version'' is heartbreaking.
- "Never Let Go" from Orphans: Brawlers, Bawlers & Bastards is another one.
- "Take It With Me" from Mule Variations can always open the ocular floodgates.
- 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 "Pay Me" from Bad As Me.
- And "Back in the Crowd" from the same album, 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 Just Friends when they've been so much more to one another.
- "Ruby's Arms," (Heartattack and Vine) "No One Knows I'm Gone," (Mule Variations) "Lucky Day" (The Black Rider), "Flower's Grave..." (Alice) The list goes on. Tom Waits' ballads will destroy your soul.
Oh Jesus Christ, this God. Damn. Rain...
- The final verse of "Ruby's Arms" is a contender for the most heartbreaking moment ever caught on tape. Even Waits is audibly choking back tears.
- "San Diego Serenade" from The Heart of Saturday Night... Just... Just "San Diego Serenade".
- "Burma Shave" from Foreign Affairs. 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...
- "Come On Up To The House" from Mule Variations, which almost perfectly describes the feeling of depression.
- "Hell Broke Luce" from Bad As Me 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" from Rain Dogs has an irrepressible melancholy to it that's impossible to shake. The final verse takes the cake, though.
"Well, things are pretty lousy for a calendar girl, the boys just dive right off their cars and smash into the street,"
And when they're on a roll, she pulls a razor from her boot, and a thousand pigeons fall around her feet,
So put a candle in the window and a kiss upon his lips, as the dish outside the window fills with rain,
Just like a stranger, with the weeds in your heart. And pay the fiddler off 'til I come back again."
- "A Little Rain" from Bone Machine.
- Reading the details of his relationship and breakup with Rickie Lee Jones counts- the two had a very promising relationship, until the runaway success of Rickie's self-titled debut album began to pile a lot of stress onto her from the sudden fame, leading her to a drug addiction that forced the couple apart. Waits would marry Kathleen Brennan a year later and change his entire musical style in part due to this. While his reinvented style led to him becoming a cult success with a lot of original ideas, it did require a rather strong love to fall apart to happen and no doubt had an impact on some of the darker themes of those albums.
- "In the Neighborhood" is rather depressing.
- While just about every song on Mule Variations is sad, a special mention goes to Georgia Lee, a song about a young troubled girl with nothing but Tom Wait's voice and a piano to paint the whole scene. The bridge and last stanza especially are nothing short of heartbreaking.
Tear Jerker / Tom Waits
About half of this innovative musician's output (when he isn't being seriously scary) can fall under this category.