My Top Ten Favorite Tom Waits Songs

I was twenty years old when I heard my first Tom Waits song. It was a live performance on David Letterman of “Lie to Me” off his most recent studio album, “Orphans: Brawlers, Bawlers & Bastards”.

I remember being fascinated by his sound and persona, two halves of what make up this musical force on stage. It has the authority of a master in full command of his craft while at the same time a special quality that feels like the orchestration is going to completely collapse at any moment. It sounds human in a way I’d never known music could. It has the same precision with emotion that Charles Chaplin and Vittorio De Sica had in the cinema.

I thought he was weird, no doubt. But as time went by, I couldn’t get the performance out of my head. So I got my hands on the entire “Orphans” album and quickly fell in love with my first favorite Waits song, “2:19”.

10. “2:19”
Album: Orphans: Brawlers, Bawlers & Bastards
Best Lyric: On the train you get smaller as you get further away, the roar covers everything you wanted to say. Was that a raindrop in the corner of your eye? Were you drying your nails or waving goodbye?

What a bold, rough, nasty, sweaty, bluesy, funky, angry, window-smashing, brick-hucking sound! This song was immediately on loop on iTunes for me for about a week. I put it on mixes for people. I kept telling people to listen to it. And almost nobody loved it as much as me, but that’s okay. I’d be foolish not to acknowledge that it’s a very specific taste. But until that moment, hearing “2:19” for the first time, I don’t think I ever heard a more perfect realization of everything I look for in a rock song.

After I listened to “Orphans” for a week or so, I decided I had to hear more. Right around this time I read an article about Waits in GQ which listed three albums of his which they deemed “essentials”. The albums were “The Heart of Saturday Night”, “Nighthawks at the Diner” and “Small Change”.

I was about to embark on a musical journey that would define my taste potentially for the rest of my life.

09. “The Ghosts of Saturday Night (After Hours at Napoleone’s Pizza House)”
Album: The Heart of Saturday Night
Best Lyric: A solitary sailor who spends the facts of his life like small change on strangers paws his inside pea coat pocket for a welcome twenty-five cents and the last bent butt from a package of Kents as he dreams of a waitress with Maxwell House eyes and marmalade thighs with scrambled yellow hair.

It wasn’t until I started listening to Waits’ 1974 Asylum release that I gained an appreciation for beat poetry and the possibilities that come with blending beat elements into other genres and mediums. Waits doesn’t sing “The Ghosts of Saturday Night”. He tells it like a great raconteur tells a story. The influence of Ken Nordine and Jack Kerouac is unmistakable, and being that this was my first exposure to such a sound, I could barely contain my excitement. Being a cinema junkie, I compared it to the feeling I got when I heard Tarantino dialogue for the first time… the feeling that I was discovering something entirely new and original, and yet so gleefully derivative and comfortable in its medium that one wonders how it could ever not have been!

08. “Eggs and Sausage (In a Cadillac with Susan Michelson)”
Album: Nighthawks at the Diner
Best Lyric: Nighthawks at the diner of Emma’s 49’er. There’s a rendezvous of strangers around the coffee urn tonight. All the gypsy hacks and the insomniacs and now the paper’s being read. Now the waitress said, ‘Eggs and sausage and a side of toast…’

Never before has the feeling of being at a twenty-four hour diner been so perfectly expressed in a song. It’s not just the lyrics (although they are immaculate). It’s the sound of the faux live crowd on this studio release. It’s the image of Tom sitting in a lonely Naugahyde booth on the album cover. This release also possibly was recorded during my favorite period in the development of Waits’ infamous growl. It hits the sweet spot between his young, smooth tone in “Heart of Saturday Night” and the demon-roar that was to follow with “Small Change”. That little bit of nasally inflection really works to this track’s advantage, in my opinion. And I’m not gonna lie — every time I find myself at the Magnolia Cafe on SoCo at two-o-clock in the morning I inevitably start hearing those timeless lyrics, “Eggs and sausage and a side of toast…”

07. “Ol’ 55”
Album: Closing Time
Best Lyric: And it’s six in the morning, gave me no warning, I had to be on my way. Well there’s trucks all a-passing me, and the lights all a-flashing. I’m on my way home from your place.

I feel like “Ol’ 55” is the perfect song to listen to directly after “Eggs and Sausage”. While “Eggs” is the happenings of the night, “Ol’ 55” is the feeling you have walking home the morning after. Anyone who has ever made the walk/drive of shame at six a.m. back to their apartment knows this feeling… this bittersweet, dreamlike, half-asleep feeling… the silence of the early morning streets contrasted with the hustle-bustle of where you just came from… your tie loosened and askew around your neck. Again, Waits uses his seemingly magic ability to bottle a very complex feeling into one four-minute song.

06. “I Never Talk to Strangers”
Album: Foreign Affairs
Best Lyric: Your life’s a dimestore novel. This town is full of guys like you. And you’re looking for someone to take the place of her. You must be reading my mail, and you’re bitter cause he left you. That’s why you’re drinking in this bar. Well, only suckers fall in love with perfect strangers.

The first duet I ever heard from Waits was the first he ever recorded. Bette Midler supplied the feminine vocals for this heart-wrenching, fly-on-the-wall scene of a man and woman flirting at a bar. This song carries much of the same emotion for me that Charlie Kaufman’s script for Eternal Sunshine of the Spotless Mind does, in particular Jim Carrey’s voice-over line, “Why do I fall in love with every woman who shows me the slightest bit of attention?” Waits acknowledges the foolhardy nature of that emotion in his lyrics, but doesn’t condemn it. Instead, he embraces the pain as a natural and essential part of human existence.

05. “Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)”
Album: Small Change
Best Lyric: It’s a battered old suitcase to a hotel someplace and a wound that will never heal. No prima donna, the perfume is on an old shirt that is stained with blood and whiskey. And goodnight to the street sweepers, the night watchmen, flame keepers, and goodnight, Matilda, too.

This is a song that many believe Tom wrote about exploring the city of Copenhagen in 1976 with Mathilde Bondo, the violinist of the duo Lasse & Mathilde. The best thing about this song to me, other than its beautifully painful melody, is the suggestion of a very special night in Tom’s life which we only have clues about. Waits himself has never confirmed nor denied the story, but it is very plausible that he and Mathilde had a romantic fling that night. But because Tom is a very private person, he changed the spelling of Mathilde to Matilda and gave the song a misleading title, making the listener believe it was the story of another Tom.

04. “Christmas Card from a Hooker in Minneapolis”
Album: Blue Valentine
Best Lyric: And hey Charlie, I think about you every time I pass a filling station on account of all the grease you used to wear in your hair. And I still have that record of Little Anthony and the Imperials, but someone stole my record player. Now how do you like that?

This is one of the saddest songs I have ever heard. My roommate Joe puts it best when he suggests that Waits creates a deeper, more multi-dimensional character in less than five minutes with this song than most films do with their entire running time. The story told in this song is heart-breaking, bittersweet, funny, cute, and devastating by the end. Tom’s performance of the song at Austin City Limits in 1978 includes a little rendition of “Silent Night” before and after the piece, and the whole thing when taken together may just be the finest live performance I’ve ever seen.

03. “Invitation to the Blues”
Album: Small Change
Best Lyric: And you feel just like Cagney, she looks like Rita Hayworth at the counter of the Schwab’s Drugstore. You wonder if she might be single, she’s a loner, likes to mingle. Got to be patient, try and pick up a clue.

Great song about the moment where you decide whether or not to pursue someone you’re attracted to. That wrestling of thoughts and emotions within yourself. You know it will hurt, but you want the hurt. The good with the bad. How much bad? Hopefully no more than there is good. But the melancholy tone in this song suggests that Tom’s character is drunk and hopeless as well, not unlike his other heroes. Also this is just one of my personal favorite Waits melodies.

02. “(Looking for) The Heart of Saturday Night” 
Album: The Heart of Saturday Night
Best Lyric: Tell me, is it the crack of the poolballs, neon buzzin’, telephone’s ringin’ it’s your second cousin. Is it the barmaid that’s smilin’ from the corner of her eye. Magic of the melancholy tear in your eye.

The idea of “looking for the heart of Saturday night” came directly from “Visions of Cody”, in which Kerouac’s eponymous hero was “hurrying for the big traffic, – ever more exciting, all of it pouring into town – Saturday night.” Waits claimed he’d written the song in five minutes. His companion in this endeavor, Bob Webb, recalls, “We struck on Kerouac’s concept of wanting to be at ‘the center of Saturday night in America. We got caught up in that literary notion and decided that each of us would create something around the theme. I drove home and stayed up all night writing a short play about some denizens of a backstreet poolroom. Some time after I left, Tom picked up a guitar and wrote the lyrics and music for ‘Heart of Saturday Night.’ He had it the next day.”

01. “Jersey Girl”
Album: Heartattack and Vine
Best Lyric I see you on the street and you look so tired. I know that job you got leaves you so uninspired. When I come back to take you out to eat, I find you dressed up on the bed fast asleep. Go in the bathroom put that makeup on. We’re gonna take that little brat of yours and drop her off at your mom’s. I know a place where the dancing’s free. Come on girl, won’t you go with me?

The best performance of this song is his duet with Bruce Springsteen, the artist who popularized the song in 1981. Where do I begin with this track? First, it was written for Tom’s girlfriend and eventual wife, Kathleen Brennan, whom he met while working on the score for Francis Ford Coppola’s One from the Heart. It’s easily his sappiest, most optimistic song, but it comes from someplace real, like he couldn’t bare to keep it locked inside any longer. This song is Tom Waits shouting from the roof of a parking structure that he’s in love.

And isn’t that all he and his work has ever been about? Love?


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