So, my friend Josh found an article stating the best 15 Tom Waits tracks. We both agreed it was pretty good, but argued it was wrong for different reasons. So the challenge was set. Draw up your top 15. You choose the criteria, and justify your choices.

I had to decide the angle - is it to initiate newbies? Show off my understanding of his artistry? Prove my fanboyness by picking the hardest to like?

The answer to all of the above is none. I picked 15 that are that punch in the chest, sit in the loft whispering, or flat out scream the loudest to be heard.  This list could easily have been 40 tracks. But it can only be 15 (I don’t make the rules!).

15. Eggs & Sausage (In A Cadillac with Susan Michelson)

Nighthawks is a “live” album, recorded over a few nights, and is Waits at the peak of his drunk hobo era. It takes the imagery from the Hopper painting of the same name, and throws it in with a load of other late night city snapshots. It’s a Waits staple - the tales of a city underbelly, told in observations of moments, all over a lazy jazz riff. So why the top 15? Authenticity. A quick glance at youtube reveals this to be uncoverable without cringing.

14. Cold Cold Ground

It’s a funeral song, it’s a love song, it tells it story through apocalyptic images, but is still intimate and personal. It’s got references to all sorts of mythologies about death, too. It’s pretty great.

13. Jersey Girl

I’m putting this straight right now - I love Springsteen. He’s great. He does working class schmaltz like no other. And yet, “Jersey Girl” showcases why Waits is not only a better writer, but performer. When Springsteen sings it, it’s another love song. When Waits sings it, it’s desperate, romantic, and evocative. It’s a story, but you’ve definitely felt what he’s singing about. Also, this arrangement. A languorous piano intro, that layers strings, then a frigging glockenspiel into it. And it sounds glorious. Eat it, Springsteen.

12. Better Off Without A Wife (Nighthawks At The Diner)

I like that this is right after a love song. What sets “Better Off…” apart is that it captures everything that is pathetic and great about being single, all in a nice simple piano hook. Desperation never sounded happier.

11. Eyeball Kid

Do you know what Ketjak is? Waits does. It’s Balinese chanting. To then layer that over a gospel sample using hip-hop principles, all to orchestrate a song about the rags to riches tale of a boy born only as an eyeball, sounds so ridiculous on paper that it couldn’t work. Not only does it, but you’ll be singing the chorus by the end.

10. Cold Water

Hobo blues. Social commentary. Gospel notes. But what sets this apart is the performance. The roaring, the subtle counterpoints behind the lead vocal, and Marc Ribot’s guitar solo, that sounds like someone stomping through a junkyard.

9. Gun Street Girl

“Gun Street Girl” was the first Waits song that really “did it” for me. It’s the simple guitar, the story, and the delivery, all tied together. There’s plenty like it in the catalogue, but none get the balance quite as right as this. Femme Fatales, crooks on the run, and a blind guy with a dog. What more do you want?

8. Such A Scream

Bone Machine is a hot mess of an album. Its death-by-percussion, scare-the-crap out of you approach doesn’t work on some of the tracks, which are derivative of better work. But sat on track 3 is this. The is a live version, and as such doesn’t quite do it justice. The composition is intricate, the lyrics incredible, and the images indelible. There’s clanking chains, rattlesnake percussion, sax that sounds like steam escaping, and a stop-start rhythm that’s sorely lacking elsewhere on the album. Essential.

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7. Shore Leave

Waits is obsessed with theatre and film. It permeates a lot of his later work. “Shore Leave” works, because it sounds like a film. Oriental percussion, the drone of what sounds like motor bikes, you can hear the rain on the streets. It sounds depraved and lonely, and then the monologue gives way to the romantic chorus. Plus cocktails and midgets in one song. “Shore Leave” is one of the most cinematic Waits tracks, and I love it.

6. Downtown Train

A Waits track with a music video? “Downtown Train” is one of the most accessible of the canon, and for a good reason. It has structure - and a chorus! It’s a love song, for that moment your heart bursts. It’s triumphant, romantic, wistful and just a little stalker-ish. Oh, and the video is awful. That’s the ’80s for you.

5. The Train Song (Big Time version)

It’s another song about trains. Well, it’s the song about trains, to be fair. It’s a story song, about running away from your life and regretting everything. It’s heart rending in the first place (the original version on Frank’s Wild Years) but the live recording on the Big Time album is like a knife to the heart. Best not to listen to it late at night.

4. Day After Tomorrow

Waits loves soldiers. From Swordfishtrombones’ “Soldier’s Things” (maudlin, saccharine and eggy) to the concussive sturm-und-drang of Bad As Me’s “Hell Broke Luce”. But it’s Real Gone’s “Day After Tomorrow” that really nails it. A beautiful guitar ballad, giving a grunts-eye view of war. It was the first overtly political song that Waits put out, criticising the reasons for being in the Gulf. The lyrics give the personal touch no one else could bring, poetic, simple and lonely. It’s a masterpiece of writing: “I am not fighting for justice / or for freedom / I am fighting for my life / and for another day in the world here”. Gulp.

3. Time

Sat in the middle of Raindogs is “Time”. It’s the centrepiece, a heap of broken images, all tying together into something more. It’s not really a love song, it’s not really a death song, it’s a unique beast. There is at least a train in it though. It’s surreal and beautiful, but dark and tragic at the same time. It’s also been covered a million times. Tori Amos’ version is the only tolerable one I’m aware of.

2. San Diego Serenade

I was all set to relegate SDS to the back end of the top 15. Thinking about it, it’s so ridiculously sentimental that it borders on trite. But it’s sincere, honest, and one of the prettiest ways of describing love in a song that you’ll ever hear. It’s straightforward, no bells or whistles. I even found a pretty live version for you to watch.

1. Christmas Card From A Hooker In Minneapolis

“Christmas Card…” is my favourite song of all time. In a list of sad songs about lives gone wrong, it sits at the top of the pile. It’s a Bukowski poem in part, but so much of it is down to delivery. It takes regret to an art form, with lost love, missed opportunities and bad luck being punctuated with hopeless dreams and blind optimism. And then there’s the sucker-punch of the last verse. Above is a live version. It starts with an off-key ramble through silent night. It’s hideous. Deliberately, I think (although you could never prove it). But by the three minute mark, you realise it’s punched you right in the life. And that’s why I love it.

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