Photo: Courtesy of Anti- Records

The 15 Best Tom Waits Songs

From apocalyptic blues boasts to backwoods chant-alongs, here are 15 of the best songs encapsulating Tom Waits’ incredibly varied career.

10. “Step Right Up” (Small Change, 1976)

Much of Small Change finds Waits dipping dangerously into zeeba-baba-doo-ba “gee ain’t I the hippest cat” territory. That said, you are a humorless prick if “Step Right Up” doesn’t astound and delight you. A litany of huckster come-ons over a dangerously limber jazz trio, “Step Right Up” is positively one of Waits’ most incredible vocal performances: it’s hilarious, it’s athletic, and it contains the indelible line, “The large print giveth, and the small print taketh away.” This live version is slower than the record as if Waits knew that was a feat he couldn’t replicate nightly.

9. “Jockey Full of Bourbon” (Rain Dogs, 1985)

Another positively iconic Waits tune thanks to its use in Jim Jarmusch’s Down by Law. “Jockey” cruises in second on hand drums, upright bass, and Ribot’s guitar set to “stun”. Waits’ vocal proves he doesn’t have to bellow to cast his spell — his sandpapery whisper paints images both baffling (“And I’ve been stepping on the devil’s tail / Across the stripes of a full moon’s head”) and terrifying (“Bloody fingers on a purple knife”).

8. “Hoist That Rag” (Real Gone, 2004)

“Hoist That Rag” sounds like it was recorded in a raft that just left Cuba. And I mean that in a good way. Listening to Waits shift between his high, keening register on the verse and that rafter-shaking bellow on the chorus is an unmatched thrill, and Marc Ribot turns in a hypnotic, catchy gem of a solo midway through.

7. “Downtown Train” (Rain Dogs, 1985)

The irony in this song being covered by Rod Stewart is that Waits’ original version comes closer to the brandy-soaked, rough-edged charm of Stewart’s early records. That’s Richard Hell and Lou Reed’s old bunky Robert Quine playing guitar, and aside from Waits’ husky, strained vocal, his guitar is the real soul of this song. “Downtown Train” is wounded, lonely, but still ultimately hopeful — Waits in a nutshell.

6. “Warm Beer and Cold Women” (Nighthawks at the Diner, 1975)

Early Tom Waits was often in danger of be-boppin’ and finger-snappin’ his way into caricature, but “Warm Beer and Cold Women” walks the line between character and caricature beautifully. It helps that Waits assembled a top-notch band of LA jazz session vets to help his song softly strut through Nighthawks at the Diner — Pete Christlieb’s deftly supportive sax and Jim Hughart’s supple bass work elevate this tune to the closest Waits ever got to pure jazz.