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Kathleen Brennan, Tom’s wife, & indispensable writing partner since the early 80’s, has classified Tom as writing two types of songs, Grand Weepers & Grim Reapers. I’ve tried to put a good mix here. Some real brawlers, ballers, & bastards (to use another TW self-description).

I kept off any of his “hits?” by proxy like OLE ’55 (The Eagles), DOWNTOWN TRAIN (Rod), BAD AS ME (Tom Jones), DOWN IN THE HOLE (recorded as theme to The Wire by a different artist each season), or his signature track, TOM TRAUBERT’S BLUES (probably his best known song, despite the incongruous title). Those are all highly recommended, & you can search them out too.

This is by no means a list of my favorites in order. Looking at my list for Volume 2, I’m just as excited! I’ve saved some of the best for later.  Playlist is the link directly below…

HOLD ON –  Busting out of a town whose motto is… “If you live it up, you won’t live it down.” Some great wisdom throughout… “If you share my bed you share my name”. “You don’t meet nice girls in coffee shops.” On the MULE tour in the late nineties, he would elongate the final word of the devastating line…“I miss your broken china voice, oh how I wish you were still here with me.” Shivers every time. “St. Louis got the best of me.” He sure names a lot of places in his songs. When asked why… “Every song needs to be anatomically correct: You need weather, you need the name of the town, something to eat – every song needs certain ingredients to be balanced. You’re writing a song and you need a town, and you look out the window and you see “St. Louis Cardinals” on some kid’s T-shirt. And you say, “Oh, we’ll use that.””

ON THE NICKEL – A Hobo’s lullaby written for a little seen indie film of the same name. This live take is from when it was relatively new. This song just floors me.

FISH & BIRD – The sad tale of a love affair that can never be realized. Don’t cry though, when it’s clear out, there’s a whale on the moon, & a bird on the tide. Another nominee for saddest song. Orchestrated so well. Is that a triangle I hear in there? And one more thing… If Tom Waits calls a whale a fish, then goddamnit, it’s a fish!

EARTH DIED SCREAMING – The apocalyptic kick-off track on Tom’s best album, Bone Machine. It’s like a voice coming up from under hell, horses (of the apocalypse) clip-clop sounds the percussive accompaniment. “The great day of wrath has come, here’s mud in your big red eye/The poker’s in the fire & the locusts take the sky.” 

TAKE IT WITH ME – Framed by an absolutely gorgeous piano melody line, this 1999 song seems to magically take us back to Tom’s early solo-troubadour days. This might be my favorite ballad of his. Imagine being so lonely that you’ve… “worn the faces off all the cards.”  The line about champagne is actually quoting Anton Chekhov’s last words. The final verse is genius, as each line contracts in on itself like a lyrical Babushka doll until all that’s left is his woman’s heart. Upon release of the record, an interviewer teared up describing the effect of this song to him while sitting in a diner. Tom’s response? Holding up 2 pieces of toast in front of his eyes, so he couldn’t see her cry. He always seems to go for a true grand piano sounds, slightly murky, not too bright like the electronic kind. Listen for them, & you can hear the piano pedals loudly through the whole thing. Yeah!

DIAMOND IN YOUR MIND – Not on any official album, just a hard to find bonus track on the mammoth ORPHANS vinyl box set. This song was donated to Solomon Burke for his comeback record about a decade ago. Tom did it live with the Kronos Quartet for a charity show that was also recorded. That’s the version here. complete with crowd sing-along, & a joke in the intro. Some great lines too. “Everything is sacred, nothing is profane/Money is just something you throw off the back of a train.”Plus, the crowd pleasing (listen to his perfect timing on the phrasing)… “She’s like a wrecking ball that’s no longer connected to the chain.”

ALICE – Title track of the soundtrack album based on the stage play telling the story of Lewis Carroll’s obsession with the real-life young girl upon he would cast into literary Wonderland. “There’s only Alice.” The skates on the pond spell her name, but trace it twice & you’ll fall through. When he compares her hair to,“meadow grass”, I thought he was saying “metal grass”, which is actually cooler (make mental note for future lyric). “How does the ocean rock the boat?/How did the razor find my throat?”

INNOCENT WHEN YOU DREAM – This is a song only Tom could’ve written, sounding like a demented Oompah Howlin’ Wolf. He said at his Rock Hall induction (after a great intro from Neil Young) that, to him, songs are just… “interesting things to do with the air.” This song floats dreamlike out of nowhere, light as a feather, then fades back into nothing, making you wonder if it was really here at all. Always a concert favorite.

BLACK WINGS – A spaghetti-Western flavored character study of a mysterious phantom figure who floats through history, rumored to have… “killed a man with a guitar string!” “When the moon is a cold chiseled dagger/& it’s sharp enough to draw blood from a stone/He rides through your dreams on a coach and horses/& the fence posts in the moonlight look like bones.” “Well they’ve stopped trying to hold him with mortar, stone, & chain/He broke out of every prison/Boots mount the staircase, the door is flung back open/He’s not there for he has risen!”

DAY AFTER TOMORROW – The second greatest anti-war song ever written (see Iron Maiden, “Two Minutes To Midnight” but that’s for a future list). Protest street cred given by Joan Baez covering it. Takes the viewpoint of a weary soldier so close to coming home. He misses the mundane everyday tasks of life, like raking leaves & shovelling snow, but over here… “I just do what I am told/We’re just the gravel on the road.” Full of hopeful anticipation, but knowing only the lucky ones make it back. “How does God choose? Who’s prayers does he refuse?”

EVERYTHING GOES TO HELL – “A man has only one thing on his mind.” Pure devil lust set to a nice Bossa Nova bounce. Unexpected modulation half way through. Tom has said… “I like a beautiful song that tells you terrible things.” This one lists the lies of the world through a misogynistic pessimist’s eyes. Advice on just who to believe in a world that…“don’t care what a soldier does in town/It’s all hanging in the windows by the pound.” Tom only wants to hear his woman… “purr & moan.” After all, she’s… “got another man that brings the money home.” Some of my favorite lyrics of his, which is saying something.

BAD LIVER AND A BROKEN HEART – Never heard a better song about wallowing in alcoholic self pity as this one. Expertly crafted. Too many great lines to quote all of them. “She was sharp as a razor, soft as a prayer.” “I’ve got my own double-cross to bear.” “You can pour me a cab, I just can’t drink no more, ’cause it don’t dowse the flames that are started by dames.” Preach Tom, preach. More from the man himself… “I tried to resolve a few things as far as this cocktail- lounge, maudlin, crying-in-your-beer image that I have. There ain’t nothin’ funny about a drunk. You know, I was really starting to believe that there was something amusing and wonderfully American about a drunk. I ended up telling myself to cut that shit out.”

WHO ARE YOU – The first Tom song that really sank its hooks into me, & still perhaps my favorite vocal performance. He has said that it’s the bitter things you say to an ex you run into at a party. “Are you still jumping out of windows in expensive clothes?” “I did my time in the jail of your arms.” “Excuse me while I sharpen my nails.” “I fell in love with your sailor’s mouth.”The lyrics in this, to me, line up perfectly with the mid-sixties acerbic Dylan of “She’s Your Lover Now.” I can even hear him singing it with the thin wild Mercury backing from Blonde on Blonde. Of course, Tom grew up putting Dylan lyrics on his bedroom walls, & later said…“For a songwriter, Dylan is as essential as a hammer, nails, & a saw are to a carpenter.”

GOING OUT WEST – Ok, let’s rock. Popular music has a long history of bragging songs, from ‘Hootchie Cootchie Man,’ to ‘I’m Too Sexy,’ to, um, what’s that one rap song? Oh yeah, all of them. In this junkyard blues, A lifetime loser looks to California’s promise of glitter dreams come true. He’ll do well out there, knowing karate AND voodoo! He’s no extra, he’s a leading man who can…“really drive a bed.” Even his parole officer would be proud of him! This 2008 live take has the funniest background vocal I’ve ever heard (not on the studio take).

WHISTLE DOWN THE WIND – I picture this song set in some remote, frozen, ice covered town. Could there be a chorus more sad than… “I can’t stay here and I’m scared to leave, just kiss me once and then/I’ll go to hell, I might as well be whistlin’ down the wind.” “The places that I’m dreaming of, do they dream only of me?” When he sings… “I’m not all I thought I’d be, I always stayed around,” it gets me every time.

WHAT’S HE BUILDING IN THERE?  Speculation runs wild with nosy neighbours. Of course, eventually you will become that creepy neighbour yourself. This spoken word piece tries to assemble a character portrait of the weirdo next door. Take it away Tom… “It’s about thinking we have a right to know. ‘Y’know, he drives a blue Mazda and doesn’t get home until three in the morning. He was karate-chopping his own shrubbery last night – in his underwear. So we put all those things together and we make up a story about someone that bears no resemblance to the truth, and then we make it a serial. And that’s what happens with the media. We love looking at each other through keyholes. They ought to make keyhole-glasses, they’d sell a million of ’em, because that’s how we prefer looking at each other, down on our knees in front of a keyhole.”

IF I HAVE TO GO – Another contender for his saddest song. “Until I send for you, don’t wear your hair that way. If you cannot be true, I’ll understand.” “I’ll leave my jacket to keep you warm. That’s all that I can do.” One of my favorite vocal melodies, & he nails it.

COME ON UP TO THE HOUSE – This live take is a one-man gospel choir tour-de-force. Mavis Staples, Sister Rosetta Tharpe, &… Tom Waits? YES! “Does life seem nasty, brutish and short/The seas are stormy and you can’t find no port.” My favorite line being… “Come down off the cross, we could use the wood.”

YOU CAN NEVER HOLD BACK SPRING – Picked because Tom sounds just like Louis Armstrong on it. Great lyrics. “The blushing rose that climbs/spring ahead or fall behind/winter dreams the same dream every time.”

JUST THE RIGHT BULLETS – From the Brechtian stage collaboration with William S. Burroughs & Robert Wilson, “The Black Rider.” Sounds like something from Germany in the ’30’s. Who else writes songs like this nowadays?! Love that staggered, drunk rhythm.

TAKE ME HOME – Written & recorded for the Coppolla flop ,”One From The Heart”, for which Tom received an Oscar nod. Most of that album was duets with the unlikely Crystal Gayle. This one is Tom alone. Does more with less than 2 minutes than most writers do with 5. “The world’s not round without you.” Aww!

LAST LEAF – This isn’t a personal favorite, but I put it on because it’s another in a long line of collaborations with Keith Richards. Tom sang on the Stones, “Dirty Work,” album, appeared onstage with them last year, & has written at least an albums worth with Keith. Back in the day, Tom said about hanging with Keith…“Sometimes you finish the song not the bottle, sometimes it’s the other way around.” You can hear how weathered they both are on this duet. Not really even harmonizing, just croaking it out with full mileage audible. This song is from Tom’s most recent album. A few tracks before this one is a song slyly called, “Satisfied,” where he barks… “Mr. Jagger and Mr. Richards will scratch where I’ve been itching!” while Keith spirals signature Tele licks behind him. Two pirates living it up. LAST LEAF though, finds the survivors pledging not to go down without a fight. “I’m the last leaf on the tree/The autumn took the rest but they won’t take me.”


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