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It was my college friend Jon who introduced me to Tom Waits. I was a freshman, and he was a sophomore, and we were hanging out a lot in those days, drinking coffee and Shiner Bock. Mostly I was waiting for Jon to decide he wanted to date me, which he never did, so we burned up hours in his studio apartment near campus arguing about theater and philosophy. On this particular night we had gotten so drunk or it had gotten so late that he made a tidy bed for me on the floor and we stayed up talking to each other across the dark.
His friend Andres was also there. Did I mention that? Well, I admit I didn’t want Andres to be there, even though I loved him (but not in that way). Still, Andres did kind of love me in that way, so there we were, a trio of thwarted desire lying in our separate beds, and that’s when Jon introduced me to Tom Waits.
It might be more accurate to say he presented me with Tom Waits. There was enough buildup for British royalty. Shhh. Stop moving. Listen to this part. Did you hear that line? I wish I could remember the song, but I suspect it was early lounge singer Tom Waits. Funny and broken and three sheets to the wind.
I don’t think I’d ever heard of Tom Waits. I was a musical theater fanatic in high school. My friend Catherine and I drove around in her Ford Explorer singing three-part harmonies to En Vogue and the “Grease” soundtrack. But I wanted to know Tom Waits, because I understood that knowing him was a tunnel to Jon, just like Ionesco, and Nietzsche, and Louis Armstrong were also tunnels to Jon. I wanted as many tunnels as I could get. So I listened with reverence, and nodded, and hoped that I could discover some element that would explain Jon to me, or help him find me irresistible. But if I’m totally honest, what I thought the first time I heard Tom Waits was: This is awful.
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A 2002 GQ profile describes Waits’ voice as a clown crossed with a cherry bomb. Waits’ music can be lovely or it can be shot through with carnival menace, but it’s his voice that is his most distinctive quality, a love-it-or-hate-it growl that is sometimes comic in its desperation. It got wilder as he grew older, and his voice serves as a kind of carbon dating system: The early ballads are a boozy baritone; the later stuff is feral. My reaction to his voice at the age of 19 was similar to my first sip of Scotch. My face puckered. I wondered how anyone could drink this stuff. But after years of listening to Tom Waits, I have come to crave that kind of brutality. (After years of listening to Tom Waits, I also came to crave Scotch.)
That GQ story is my favorite profile of Waits. It’s written by Elizabeth Gilbert, who went on to pen a blockbuster memoir about eating and praying and loving. But back then, she was a magazine writer fascinated by masculinity. She wrote a few books on the subject, which I’ve heard are good, and her piece on Waits fits into that puzzle, because he is an off-center, darkly poetic masculine hero. Before I ever loved Tom Waits, I loved guys who loved Tom Waits, and they had certain qualities in common. They all smoked cigarettes (often unfiltered). They loved booze (often whiskey). They drank coffee (black). They had flourishes of eccentricity: A fedora worn to the grocery store, a chain wallet, a deceptively casual method of cupping a flame as they lit a cigarette against the wind. They were reckless and tender and sullen and, good god, they were beautiful. The chips were stacked very high against me back then.
In my sophomore year, I fell in with a guy who practically worshiped at the house of Tom Waits. He and his gang of angry young men (which is what we called them) moped around campus with creative facial hair and a disaffected slouch that marked them as different from other kids who came from the suburbs of Houston and Albuquerque. “I’m interested in the commodification of violence,” one of those guys told me, stabbing the air with his smoking hand, and I went home and wrote it down, because it sounded so cool.
I listened to 10,000 Maniacs — classic, awesome nerd-girl band — and around that time Natalie Merchant recorded a cover of Tom Waits’ “I Hope That I Don’t Fall in Love With You,” and the first time I heard it, my breath caught in my throat. It was so fragile, so perfect. “Well, I hope that I don’t fall in love with you / ‘Cause falling in love just makes me blue.” That’s exactly how I felt about the guy, who had sidled up to me at a party, and we had fallen into each other’s bodies in that slumping, slightly meaningful way, and the next day I woke up newly tangled about him, experiencing deep revelations about how gorgeous his eyes were, etc., etc., and all I could think was: No no no, not this again.
That song is one of the greatest ever written about the fleeting romance of last call, the way a dim bar and a bottle of Jack Daniel’s can conspire to make you believe you have lived lifetimes without ever rising from your seat. At the time, I did not quite understand this, but I would spend the next two, 10, 15 years of my life figuring it out.
The guy scoffed at the Natalie Merchant cover. How could a woman like her sing about drinking stout, about “these old tomcat feelings you don’t understand”? I swapped Natalie Merchant’s version in my five-CD changer for the soft grumble of the original, and I never looked back. The guy and I didn’t work out. But I had it bad for Tom Waits.
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I scored points with my next boyfriend for name-checking Tom Waits in an early conversation. The right guy would fall to his knees if you told him your favorite song was “Ol’ 55.” The acquisition of such knowledge was the upside to these botched romances. You would go into a relationship one person — an English major with a kink for Tom Wolfe and ’70s soul — and you would exit with a new list of names piled on your coffee table: Frank Sinatra and Joan Didion and the Violent Femmes. Your heart might be dripping from between your fingers, but hot damn, your CD collection was good.
This boyfriend was the guy who truly made me understand Tom Waits. Not because he explained him to me — the way he explained how to line up a shot in pool, or how to blow a smoke ring — but because I was crazy about him, and he broke up with me a month after we moved in together, and in the six months — OK, a year — after he left, Tom Waits became the soundtrack to my sadness. All those weepers about loving someone who left, leaving someone you still love, all the ragwater and bitters and blue ruin.
I listened to female singers, too. They were a pipeline to rage and melancholy — Tori Amos, Liz Phair, Billie Holliday — but I didn’t seek catharsis so much as I sought to understand, to sift through the wreckage and find some lesson here. Why did he leave me? What had I done wrong? And so on the nights when I felt like running my fingers over those scars I listened to Tom Waits, “The Early Years, Volume One.” I listened to the last track, “Old Shoes and Picture Postcards,” on repeat.
So goodbye, so long, the road calls me, dear, and your tears cannot bind me anymore
And farewell to the girl with the sun in her eyes, and I’ll kiss you and then I’ll be gone
When I listen to that song now, I hear the same desperado cliches I know from a hundred country ballads. But back then, the words were a revelation to me, the final piece of a complex algorithm. You guys, you guys, I got it: He had to leave me, it was destined somehow, locked in our DNA that I would be the one standing on the balcony in my bare feet with tears streaking my face and he would be the one driving off into the sunset in his 1995 Honda Civic, flicking a Camel Light out the window. (This never happened, by the way.) Of course, there were other reasons for our rupture: He had quit drinking, and I had not. He was out of college and finding his way in the world, and I was pouring beer on people’s heads at my birthday party. He needed space, and I longed to be smothered.
But at the time, it was unfathomable: He kissed me, and then he was gone, and I spent the next six months — OK, a year — sleeping with him anyway, trying to get back some of the sunshine and safety I’d felt in his presence and feeling let down all the time. I wrote and produced a play inspired by losing him — it wasn’t about him, but then again, it was entirely about him — and every single night before the curtain rose I would comb the audience from backstage trying to find his face, waiting for the sick electric jolt I would experience when I saw him sitting there. And every single night he would not be there, and I would experience a wave of rejection before the show even began.
After the last performance, I got wasted on a Sunday afternoon. What else could I possibly do? I wanted to know. I fucking wrote a play about him, and he did not come. It seems obvious now: Of course he would not come. Of course he did not want to interrupt his busy life as a newly minted chef to sit in a drafty auditorium and watch some bizarre simulacrum of our time together. But I wrote with the idea that the sheer force of my desire could change his mind. I wrote short stories. I wrote letters I never sent. The thing is when we’re wounded everyone’s a bit insane, Tom Waits sang, and I lived it, man. And what I never stopped to appreciate amid all the soggy tissue and melodrama was that he had given me something far more extraordinary than a college relationship. Fifteen years later, the framed poster for that play still hangs in my hallway, one of the proudest moments of my life. That guy — I think I have his photo in an album, somewhere.
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Waits is such a guy’s guy that it takes a certain kind of woman to love him. I grew up in awe of my older brother — his music was the first guy’s music I ever learned — and part of my story has been an urgent wish to have the same shambling adventures as the men in my life. I wanted to jump off balconies and stagger through the streets of some foreign town, shirt stained with blood. I wanted to pour Bushmill’s down my throat and light myself on fire. I knew every word to the song “Pasties and a G String,” a winking, bawdy ode to the low-rent freedom of live nude girls. In the year after college, I went with a male friend to a strip club — one of those junky roadside joints — and I had this idea that I would run my eyes all over those women, I would devour them, but instead I felt strange and wrong inside, and I made him give all his dollar bills to the heavy women and the older women no one paid attention to, and I went home that night and lay alone in bed feeling so blue. (Because I wasn’t one of those women? Because they were?)
It was hard to find my place in those songs, and in the macho novels I was obsessed with (books about war, books about madcap travels, books about drink and damage). What I never realized — what never occurred to me — was that Tom Waits’ greatest collaborator was his wife, Kathleen Brennan. A former movie executive wary of the spotlight, she has co-written much of his work since “Swordfishtrombones” and in his rare interviews, he speaks of her with genuine warmth. “I’d be working in a steakhouse if it wasn’t for her,” he says in the GQ article. “I wouldn’t even be playing in a steakhouse. I’d be cooking in a steakhouse.”
Maybe that’s what I needed: my own Kathleen Brennan. And where do you find them, anyway? Waits attributes Brennan to cracking open his sound, but it was no doubt her stability that enabled such a grueling, decades-long career in the sideshow. Every sinner needs a saint, or something like that. For a guy who used to fall off piano benches, Tom Waits looks pretty healthy in his old age.
In 1999, I saw him when he played at SXSW in the most-coveted showcase of the year. To say it was a spiritual experience feels too small. It was the best live music show I’ve ever seen, and I can’t imagine I will ever see a better one. I sat in the first balcony with a spectacular three-beer high — not drunk enough to be gone, just drunk enough to be right there — and I remember thinking how booze and music and storytelling were like God. Or maybe I should say: If that’s all God was, it was still a lot.
At 28, I fell in love with a guy who listened to Tom Waits. Of course I did. I assumed that every man I ever loved for the rest of time would be as besotted with Tom Waits as I was, just like he would be as besotted with booze, and cigarettes I could bum from him, and impulsive late-night trips to nowhere in particular, a night and a hangover we could share.
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The next boyfriend was the ultimate Tom Waits boyfriend. He was a homicide detective in New Orleans. He was handsome and solitary. He told me stories about prostitute sweeps in the French Quarter and what it felt like to touch a brain. Decades of kneeling at the altar of such grimness was no doubt part of why I fell for him in the first place. I love gangster movies where everyone dies in a hail of bullets. My favorite show of all time is “The Wire.” It was one of a hundred reasons our romance felt written in the stars to me, but the funny thing about the ultimate Tom Waits boyfriend is that he had never actually heard of Tom Waits.
He liked the Eagles. “I can’t stop listening to this song ‘Hotel California,’” he said to me once. “Have you heard of it?”
“In the seventh grade, baby,” I said, and ran my hand across his cheek, and he gave one those twisty little grins he offered when he felt slightly self-conscious. He didn’t pay much attention to music, or movies; they were necessary distractions from the soul-suck of the murder police. During the holidays, he kept the radio on the Christmas music station all the time (it drove his partner crazy).
But I knew he would love Tom Waits, just like I knew I would move to New Orleans and we would get married and have adorable babies with twisty little grins. I sent him “Small Change” with a note that said, “I am honored to give you your new favorite album.”
I went even further than that, actually. The first time I visited him in New Orleans, he took me to a bar where the cops hang out. (“Don’t mention you’re a journalist,” he said, which was a joke, but not really.) It was one of those epic nights. The whole bar singing to the Pogues. And when I got back to New York, I sent a gift to the guy who runs the place. Two Tom Waits albums, because the jukebox had a few empty sleeves, and I wrote something like, “These CDs are looking for a home in a smoky dive bar in the French Quarter. Maybe you can help them out.”
I was so pleased with myself, but it didn’t go the way I planned. The guy who runs the bar is a big Irish cop with a mustache — he is exactly the person you see in your head when I say “Irish cop” – and the next time I saw him at the bar, he said to me, “Yeah, I listened to those CDs you sent. They sucked.”
I laughed, but I was scrambling to cover up my embarrassment. How could I have misjudged this so badly? I clapped my hand on his shoulder. “I feel like I’ve given you a fine Scotch, and you’ve pissed all over it.”
He looked around. “Do you see any fine Scotch around here?” He stuck his cigar back between his teeth. “Van Fucking Halen,” he told me, and walked off.
So there you go. There is a world of difference between the men who love Tom Waits and the men who live the life he writes about. When the detective broke up with me, four months later, it occurred to me I was on the wrong side of the divide.
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In 2006, Tom Waits appeared on “The Daily Show.” Jon Stewart seemed uncharacteristically nervous. “I was struck when I met your wife, your family, how unbeaten by life you are,” Jon Stewart said at the top of the interview. “I used to listen to your music and think, boy, I’d like to lie in the street nearly dead with that guy.”
Waits nods. “It’s an act,” he says.
And I remember feeling weirdly betrayed by that. I mean, I knew it was an act, but maybe I didn’t? Nobody can ravage their body the way he purported to and then stick around for four decades. So of course Waits was sober. Of course he no longer smoked. But it was impossible to imagine him without the neon glint, the clang of empty bottles in the background. Consider: Tom Waits on a treadmill. Consider: Tom Waits juicing. Consider: Tom Waits, happy family man.
It was impossible to imagine my life without such wicked accouterments, too. I put off quitting drinking for as long as I could, but in 2010, I had to stop before my life tipped into parody, the 36-year-old drunk woman all dressed up and falling down. Since then I have been forced to wrestle with so many false delusions, like the one in which every romance comes with a pack of smokes, or the one in which I spend each night sinking into a vodka tonic, cold and fizzy and fantastic.
Sometimes I feel embarrassed that I loved Tom Waits so much. I talk to cool women who defined themselves by the riot girl sound, or Patti Smith, and I think, why wasn’t I like that? Maybe the embarrassment I feel isn’t about Waits at all. It’s about the girl who tried so hard to be someone she wasn’t, the girl who languished in her own self-pity, who posed so many ways for those boys to see. Those boys are all nearing middle age now. They have wives and children and mortgages and, if I had to guess, some nicotine gum lying around somewhere. I’m still friends with most of them. I wonder what they hear when they listen to Tom Waits.
I’ve heard that Waits doesn’t like those old songs, the songs pre-Brennan, and I wonder if what he feels is the tweak of regret and loss we all feel when we stumble on old pictures of ourselves. Not long ago I found a cache of them — me with a Marlboro Light in one hand and a giant margarita glass tilted dangerously in the other, me with a Dos Equis wearing a see-through undershirt staring at the camera like I’m trying to start a fight — and I laugh at those pictures at the same time I feel grief, and this is one of the qualities in Tom Waits I have long appreciated, the way a good feeling can get wrapped up with a painful one. I feel sad for all that I didn’t know then, but I feel grateful that I forged ahead anyway. I feel sad that it’s gone now, but grateful that I had it. I feel sad that I spent so many hours wanting those guys to love me in a certain way — all that time and energy and agony wishing the world could be something it was not — but I feel grateful that they did love me, all of them, in the way they knew how.
Sarah Hepola is an editor at Salon. Her memoir, "Blackout," will be published by Grand Central in June.More Sarah Hepola.