Tom Waits: His Top 20 Saddest Songs

When I was putting together my forty saddest songs list, I found it colossally difficult to limit myself to include only three songs by Tom Waits. In fact after the list was done, I was having a discussion with a friend of mine about it and I told him how I found myself constantly thinking of Waits songs, when he jokingly suggested I should’ve done the top forty saddest songs just by him. Well, I think forty might be pushing it a bit, so here are my top twenty saddest songs by the master, the genius, the incomparable Tom Waits.

20. (1975)
Album: Nighthawks at the Diner
This is the saddest song ever written about breakfast. It perfectly captures the melancholic alienation of sitting at a counter of the corner diner at 3:47am.

19 (1983)
Album: Swordfishtrombones
This wistful march is an ode to the unexplored side streets and unexamined lives of your local neighbourhood. Its music is stirring and yet has an unmistakable yearning, it’s hard to define exactly what makes you a little blue about this song, but it does.

18. (1980)
Album: Heart Attack and Vine
That piercing trumpet, underscoring this heartbreaking ‘goodbye’ song punctuates this classic scenario with its slightly classical melodic approach. You’re not sure if he’s talking about a prostitute or a girlfriend…or both, adding a broken down quality to the song.

17. (1980)
Album: Heart Attack and Vine
We all know Bruce’s version so well that many people don’t even know Waits wrote it. Personally I like Tom’s version better (although Bruce does it well) I think there’s definitely more irony and heartache in the original.

16. (1999)
Album: Mule Variations
This offering of Waits has a nice country feel to it, and gorgeous lyrics with lines like, “I miss your broken china voice” and ”He gave her a dime store watch and a ring made of spoon”. It’s like an intellectual Hank Williams song.

15. (1976)
Album: Small Change
This genius story 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.

14. (1985)
Album: Rain Dogs
Waits literally sounds like a gut shot hound in this one, it’ll tear your heart out. In these times with so many people either out of  a home or unsure whether they can keep one, this song really explains that home is only where you are at any given time.

13. (1988)
Album: Big Time
This tune has a touching European vibe to it which fits with the tone of his guitar and gypsy like mysterious lyrics. This is shadowy waits, evocative and unsettling.

12. (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.

11. (1983)
Album: Swordfishtrombones
They lyrics are so beautifully written, they literally place you in the scene – you’re instantly transported. In the end, we’re all just a collection of junk to be thrown out in a flea market after we’re gone.

10. (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.

9. (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” always get me straight in my chest.

8. (1973)
Album: Closing Time
This early work of Waits which exquisitely recalls the kind of yearning only youth can know. The older you get, the more it feels as if you’re a stone in a tumbler – smooth as glass.

7. (1985)
Album: Rain Dogs
With lyrics straight out of a Steinbeck novella, the heavy, dank cheerlessness permeates this creaky work of genius, leaving the listener forlorn in its wake.

6. (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” That’s one of the greatest lines ever… This is the ballad version of a “drunk text”

5. (1974)
Album: Heart of Saturday Night
This song is a 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.

4. (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.

3. (1976)
Album: Small Change
This is an amazing noir-ish masterpiece, like an entire Bogart movie in 3 minutes. Concentrated goodness.


2. (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, and when this last scene ended and the song came up, I actually saw grown men bawling in the movie theatre, I’ve never seen anything like that before or since.

1. (1999)
Album: Mule Variations
When you listen to this one you’re left blubbering like a gut shot hound. This is Waits stripped down to the bone, he’s just singing to his wife from his heart and we’re lucky enough to be able to listen in

15 Comments for “Tom Waits: His Top 20 Saddest Songs”

  1. Dave Kopperman

    “Tom Traubert’s Blues” will be forever ruined for me by John Malkovich, who used the lyrics ‘And it’s a battered old suitcase to a hotel someplace/And a wound that will never heal’ to describe Uma Thurman, in a Rolling Stone profile from waaaaaaay back. It struck me as the perfect combination of pretentious and creepy on his part, since a) she was 17 at the time and he was 36, and b) the focus of the article was basically about how nice her tits were.

  2. The Zeitgeisty Report (c)

    I remember that article.. her rack was pretty glorious

  3. Gábor

    Nice list, but I miss a fav of mine, Grapefruit Moon :)

  4. The Zeitgeisty Report (c)

    yeah, good call… that’s a beautiful one… Couldve easily gone on the list

  5. Rev. Dom

    I really like this list but where the f**k is “Martha” & “Train Song”. Train song describes my life to a T and I can’t even listen to “Martha” ‘s last verse.

  6. RA

    Definitely needs Martha and Green Grass is a sad one as well.

  7. Ade

    Here’s another two…. Alice and Poor Edward… a bit surprised they didn’t make it to your list, but 20 is a tough job :)

  8. I.

    Just wanted to throw out On the Other Side of the World. It’s often overlooked as its the only song other than Good Old World off of an otherwise wholly acoustic album but, for me, it may just be the best song Waits has ever written (and as a huge fan of all of Waits work, I do not say that lightly).

  9. kc

    wow!! what happened to ” on the nickel ” ???

  10. nr

    what about “If I have to go”???

  11. Patrick mc Loughlin

    You should have done 40 songs because I can’t believe Kentucky Avenue is not here or Whistle Down the Wind. In the Neighbourhood has always reminded me of Sunday afternoons as a child with no one to play with. Have no idea why. Also ‘November’ may not be so sad but its one of the best desolate winter songs ever penned. Great to see a list like this though. I had a thing for Uma Thurman’s rack as well. Didn’t we all.

  12. JBhutto

    Cold Cold Ground would probably top my list. Also needs Dirt in the Ground. Alice is pretty depressing as well. And Georgia Lee. But yeah this could go on.

  13. Francois

    Slight oversight. The 78 recorded version of ‘Innocent When You Dream.’ -Frank’s Wild Years

  14. CF

    “No one knows I’m gone”. The end.

  15. Matt Z.

    Great list! Tom Waits is incredible. I believe Lonely should be # 1. Saddest song I’ve ever heard. I put it on everytime I need a good depression. Also agree with Patrick, Kentucy Avenue is phenomenal, and incredibly sad, but it’s just a matter of opinion, and how a particular song hits you. Anyway, at least we all agree that Waits is a legend.

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