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13 Essential Lesser-Known Songs From Tom Waits’ Catalog

Tom Waits has been rolling out remastered versions of his entire catalog, spanning from his days on Asylum Records to his current home on ANTI-. The results are a terrific way to discover or revisit his work, which ranges from sentimental ballads to juke-joint blues to head-scratching sound collages and back again.

He began his career as the 1970s’ finest method actor, living on the road and sleeping in seedy motels to cultivate an image as a boozy troubadour. For his first live album Nighthawks at the Diner, Waits went as far as transforming Los Angeles’ Record Plant studios into a smoky after-hours club; according to that album’s producer, Bones Howe, “We set up a bar, put potato chips on the tables. I remember that the opening act was a stripper. Her name was Dewana and her husband was a taxi driver.”

Waits got a lot of mileage out of portraying himself as the lovechild of Charles Bukowski and Captain Beefheart, singing his blood-and-whiskey tales of alcoholics, truck drivers and forbidden lovers over pointedly out-of-tune piano. But something changed around 1976. After living that life to the hilt and doing it all for the songs, he realized alcoholism and vagrancy wasn’t all fun and games. While cutting his first great album, Small Change, he had second thoughts. “I was really starting to believe that there was something amusing and wonderfully American about being a drunk. I ended up telling myself to cut that shit out.”

After a few lovely but slightly half-hearted albums of a similar style for Asylum Records, Waits married his silent-yet-crucial creative collaborator, Kathleen Brennan, and introduced his Tom 2.0 phase. The results were stunning. For once, Waits wasn’t writing specifically about vagrants and drunks — he was writing about everything. For the rest of his career, his purview expanded to include rock’s most bizarre extended cast of freaks and misfits possible, introducing the world to Table Top Joe, the Eyeball Kid and the Bride of Rain Dog. He could write down-to-earth, with some of the most intricately detailed female characters in anyone’s songbook, or he could extol the joy of roasting a hog on a boxspring with your buddies. Waits found a common humanity in all of it.

In honor of Waits’ reissuing of his entire album catalog throughout the year, here are some lesser-known gems from his inimitable body of work.

“San Diego Serenade” (from The Heart of Saturday Night, 1974)

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Waits’ debut, 1973’s Closing Time, contained some enduring tunes like “Ol’ 55,” but he wasn’t quite himself yet. The record company wasn’t quite sure what to do with him and added unnecessary string parts and cameos from The Eagles. Its follow-up, The Heart of Saturday Night, was the first real stirring of an authentic Waits, with some elements of blues, jazz and poetry seeping in for the first time. “San Diego Serenade” is one of his most tender ballads, one which takes a hard look at what we don’t know what we have till it’s gone. Plain and simple.

“Jitterbug Boy” (from Small Change, 1976)

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Has any dispatch from a strange deadbeat played out like a brief history of the 20th century like this? Because Waits’ barfly character in “Jitterbug Boy,” found here “holding up a lamppost,” claims he’s had a pretty eventful life. Claims of dubious veracity keep coming. He fought Rocky Marciano. Played Minnesota Fats. He taught Mickey Mantle ev-’ry-than’ that he knows. Whether or not you buy these dubious cock-and-bull claims is on you, because buddy, he’s done it all. Never has a Waits song been constructed on so many unreliable sources, so magically.

“A Sight for Sore Eyes” (from Foreign Affairs, 1977)

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Hung on the melody to the traditional “Auld Lang Syne,” “A Sight for Sore Eyes” is a sweet, bumbling reunion of two old buddies among the void of absent friends. Where did the old gang go? Nash was killed in a crash. Another, unnamed, is married with a kid and she split up with Sid, who’s “up north for a nickel’s worth.” There’s no wit, no poetry, no big realizations — the guys just play a little pinball and keep the drinks flowing. It’s a touchingly relatable ode to how our relationships change as we get older.

“Underground” (from Swordfishtrombones, 1983)

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Waits married Kathleen Brennan in 1980, a creative and romantic partnership that split his life and work into two halves. Said Waits about his better half, who never appeared onstage and very rarely in photos: “She doesn’t like the limelight, but she’s an incandescent presence on all songs we work on together.” In a swift 180, Waits’ first album since the wedding didn’t start with some lovelorn, bruised ballad. Throwing out the piano in favor of an odd plink-plank of kettle drums and marimba, “Underground” is a nightmarish ode to the subterranean realm of insects, a topic he’d lovingly return to again and again. “Underground” remains a delight because Waits seems legitimately unnerved by his unfortunate discovery of a world run by bugs — “They’re alive, they’re awake/ While the rest of the world is asleep!”

“9th and Hennepin” (from Rain Dogs, 1985)

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Less a song than a monologue, “9th and Hennepin” paints an unforgettable picture. In an interview with SPIN, Waits recounted the story of a fateful day he spent on that Minneapolis street corner: “I was on 9th and Hennepin years ago in the middle of a pimp war … and at this donut shop, these three 12-year-old pimps came in in chinchilla coats armed with knives, and uh, forks and spoons and ladles … and were answered by live ammunition above their heads.” Whether or not this story has been a bit exaggerated, Waits’ imagery here will stick with you, from “donuts that have names that sound like prostitutes” to “the broken umbrellas like dead birds.” The autobiography is beside the point; in any slightly “off” location you find yourself in alone at night, there’s trouble at 9th and Hennepin.

“I’ll Take New York” from Frank’s Wild Years, 1987

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Call it Waits’ demented tribute to his influences. A mix between a ballad Frank Sinatra would sing a la “New York, New York” and the Hindenburg crash, Waits croons out of tune about drinking Manhattans and tipping the newsboy to horror-show organ and horrifying saxophone while the entire arrangement crashes and burns spectacularly. Imagine the Rockettes getting in on this one.

“Dirt in the Ground” from Bone Machine, 1992

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Waits rang in the ‘90s by finding the perfect location to record a bunch of death songs in: a part of the Prairie Sun Recording Studios building in Cotati, California, that Waits recalls was “just a cement floor and hot water heater. OK, we’ll do it here.” Waits’ catalog was getting pretty strange by 1992, but the songs that came from that cement floor had no precedent. “Dirt in the Ground” can only be described as a naked, wailing ode to the common grave of humanity. “We’re all chained to the earth and we all gotta pull,” gulps Waits, his voice cracking like he’s singing through choked tears. Almost in spite of itself, “Dirt” is not uncomfortably depressing but startlingly giddy, even as Tom wails in our ear that we’re just topsoil waiting to happen.

“‘Tain’t No Sin” from The Black Rider, 1993

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If you want to hear William S. Burroughs sing the Great American Songbook with a faint grasp of melody or good sense, apply here. Waits follows along gingerly with his Emax sampler, seemingly playing a different song. Nobody remembers The Black Rider, the Robert Wilson play “‘Tain’t No Sin” belongs to, but its 1993 soundtrack is a nice reminder that Waits and Burroughs were briefly a match made in hell.

“Georgia Lee” from Mule Variations, 1999

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Whatever you like about Waits, 1999’s Mule Variations offers a lot of it, and that’s no exception with the tenderest side of his music. “Georgia Lee,” which grapples with a real-life young girl named Georgia Moses who was kidnapped and murdered in Northern California with no suspects found, may be the most moving ballad he ever penned; it has the capability to shake you to your core. Waits doesn’t deal in sanctimony; he only pleads and wonders. “Why wasn’t God watching?/ Why wasn’t God listening?/ Why wasn’t God there?”

“Kommienezuspadt” from Alice, 2002

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A low-key follow-up to Mule Variations, Alice was written for another play of the same name. More importantly, it depicts Waits going even further off the deep end, whether breathlessly exhorting listeners “Everything you can think of/ Is true!” or singing about birth defects and red-light districts. “Kommienezuspadt,” an unforgettable track of Waits bellowing in fake German to a ridiculous oompah beat (“Sei punktlich! Sei punktlich!), is the point where analysis fails and a belly laugh begins.

“Circus” from Real Gone, 2004

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Waits’ catalog has been full of these spoken-word pieces since at least Swordfishtrombones’ “Shore Leave,” but “Circus” is something special. You can smell the sawdust in the air. But beware, for there are questionable characters on this fairground, with Waitsian names like Horse Face Ethel and One-Eyed Myra. Waits is totally in his element, relishing the details: There’s “a little bubble of spittle on the nostril” of Yodeling Elaine, the Queen of the Air, and the “music is like electric sugar.” And I don’t think anyone wants to know how Tripod the orangutan got his name.

“Army Ants” from Orphans: Brawlers, Bawlers and Bastards, 2006

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It’s time for a lecture from Mr. Waits on the copulative mechanisms of beetles, everyone. One of the strangest cuts from Orphans, an odds-and-ends collection spanning everything in Waits’ catalog that, according to him, had “fallen behind the stove while making dinner” rather than making it onto proper albums, “Army Ants” is one of the most fascinating curios in a collection full of oddities and surprises. Waits was born to intone things like “As we discussed last semester, the army ants will leave nothing but your bones. Perhaps you’ve encountered some of these insects in your communities.” Listen closely: you might even learn something.

“Talking at the Same Time” from Bad as Me, 2011

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Bad as Me doesn’t have any significant departures from Waits’ sound except for the great “Talking at the Same Time,” which Waits sings completely in falsetto over a stoned, swaying reggae beat. It’s akin to time slowing down, for really soaking in your surroundings, with Waits laying down some latter-day wisdom: “Ain’t no one coming to pull you from the mud/ You gotta build your nest high enough to ride out the flood.” Waits made a career by taking an unflinching look at humanity at its bleakest and most banal, but after all these years, he’s still offering a prettier, weirder view above it all.

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