It’ll get you, life. It’ll wear you down to a nub if you’ll let it. The only way to survive is to get in touch with your sensitive side every now and then, and just have yourself a good old bawl. Like they told us when we were kids in Free To Be You And Me — it’s alright…to cry. Personally, when I need let it all out, Tom Waits is my go to guy. There’s just something about the ragged beauty in songs that speaks to me. The collection below, in my considered opinion, are his 20 saddest. So, get out your Kleenex, pour yourself a drink and start blubbering.

  1. Eggs and Sausage (1975)

Album: Nighthawks at the Diner

This is the saddest song ever written about breakfast. It perfectly captures the gorgeous melancholy of sitting at the counter of your corner diner at 3:47am.

  1. In the Neighborhood (1983)

Album: Swordfishtrombones

This wistful waltz is an ode to the unexplored side streets and unexamined lives of your local neighbourhood.

  1. Ruby’s Arms (1980)

Album: Heart Attack and Vine

In this heart breaking farewell, you’re not sure if he’s talking about a prostitute or a girlfriend…or both.

  1. Jersey Girl (1980)

Album: Heart Attack and Vine

We all know Bruce’s version so well that many people don’t know Waits wrote it. Personally I like Tom’s version better, it’s less idealized and more real.

  1. Hold On (1999)

Album: Mule Variations

With lines like, “I miss your broken china voice,” and “He gave her a dime store watch and a ring made of spoon” how can you go wrong? It’s a thinking man’s country classic.

  1. Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen) (1976)

 Album: Small Change

This sad tale of a broken hearted man out on a late night crawl soaked in whiskey and blood is definitely in Tom’s top ten, the way he uses “Waltzing Mathilda” as the theme and the name of the woman who did him wrong…pure brilliance.

  1. Anywhere I Lay My Head (1985)

Album: Rain Dogs

Waits literally sounds like a gut shot hound in this one, it’ll tear your heart out. Tom understands that ‘home’ is a mere concept – you carry it around with you everywhere you go.

  1. Strange Weather (1988)

Album: Big Time

This tune has a touching European feel to it which fits with the tone of his guitar and mysterious gypsy lyrics. This is Waits at his most evocative and unsettling.

  1. Who Are You (1992)

Album: Bone Machine

I always thought that this song was written about Rickie Lee Jones, but I could be wrong. The line, “Well I fell in love with your sailor’s mouth and your wounded eyes” just sounded like Jones to me.

  1. Soldier’s Things (1983)

Album: Swordfishtrombones

The lyrics are so beautifully expressed. In the end, we’re all just a collection of junk to be thrown out in a flea market after we’re gone.

  1. I Never Talk to Strangers (1977)

Album: Foreign Affair

This is a great song off of ‘Foreign Affair’. On the album he does it as a duet with Bette Midler, who’s excellent. The interplay between those two is priceless, making you wonder why they never did anything else together.

  1. Come On Up to the House (1999)

Album: Mule Variations

A heart-breaker. Every time I hear this song, it’s as if he’s speaking to me and it never fails to bring a tear to my eye. The lines “The only things that you can see is all that you lack” and “Come down from your cross we can use the wood” hit me right in the solar plexus.

  1. Lonely (1973)

Album: Closing Time

This early work of Waits exquisitely recalls the kind of yearning only the young experience. When you get older, you just become a tumbled stone – your edges ground smooth as glass.

  1. Time (1985)

Album: Rain Dogs

With lyrics straight out of a Steinbeck novella, a dank cheerlessness permeates this creaky work of genius, leaving the listener forlorn in its wake.

  1. Bad Liver and a Broken Heart (1976)

Album: Small Change

“And this epitaph is the aftermath, yeah I choose my path, hey, come on, Kath,
He’s a lawyer, he ain’t the one for ya.” One of the greatest lines ever — a drunk text in song.

  1. San Diego Serenade (1974)

Album: Heart of Saturday Night

Another masterpiece written by Waits when he was just a romantic kid. It’s sad and reflective and he brings an insight to matters of the heart which are astounding for someone so young.

  1. Christmas Card from a Hooker in Minneapolis (1978)

Album: Blue Valentine

Watch this clip of Waits playing this song to a crowded room of insufferable hipster douchebags. They laugh like muldoons at the melancholy wit until they realize that this song is actually horribly depressing. It’s kind of funny to hear them shut up at the end.

  1. Invitation to the Blues (1976)

Album: Small Change

This is an amazing noir masterpiece, like an entire Bogart movie in three minutes. Concentrated goodness. 

  1. Good Old World (Waltz) (1992)

Album: Soundtrack to Night on Earth

This is from the movie Night on Earth by Jim Jarmusch. I actually saw this in the theatre when it came out, this song comes up as the last scene ends – I turned to my right and a grown man was openly weeping. I must admit, so was I.

  1. Take It with Me (1999)

Album: Mule Variations

Speaking of tears, this one will definitely turn on the water works. It’s Waits stripped down to the bone, he’s just singing to his wife from his heart and we’re gifted with opportunity to listen in


If you enjoyed this list take a look at some others we have on The Z Review!

The Top Ten Most Overrated Albums Of All Time

The Top Ten Most Overrated Drummers Of All Time

Top Underrated Bands Of All Time

The 40 Saddest Songs Of All Time

Progressive Rock for Indie Rock Snobs: A Playlist

The Top Five Most Overrated Bands Of All Time

…And all the goodies in our Entertainment  and Features sections!


About Author

I'm a writer/editor with a penchant for saddle shoes, pontification and fried pork rinds. Equal parts gadfly, cut-up, provocateur, philosopher, and silly-willy. My personal heroes include Reggie Jackson, Elvis Costello and Philip Roth.


  1. How on Earth is Train Song NOT on this list, let alone in number 1?

    I remember when I left without bothering to pack
    Don’t you know I up and left with just the clothes I had on my back
    Now I’m sorry for what I’ve done and I’m out here on my own
    It was a train that took me away from here
    But a train can’t bring me home

  2. I’d add ‘Green Grass’, and although it’s an instrumental rather than a song, ‘Rainbirds’, some great choices though

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