6. Real Gone, 2006

Real Gone is an experimental work, even by Waits' standards. He ditches the piano in favor of looped samples of his own beatboxing, and even includes turntables on a few songs, courtesy of son Casey. It also contains his most explicitly political songs in "Sins of the Father" and "The Day After Tomorrow," the latter one of the most affecting songs ever written from a soldier's point of view. "Hoist That Rag" is a particularly heavy song with a deceptively simple guitar solo from long-time collaborator Marc Ribot, while "Don't Go In to That Barn" is just plain frightening, featuring lyrics like "When the river is low they find old bones / And when they plough they always dig up chains."

Listen: "Hoist That Rag"

 

 

5. Closing Time, 1973

Though Waits' first album literally sounds like the work of a different person, within this hunk of ‘70s strings and tender L.A. balladry, Waits was dropping some real gems. "Ol' 55," which was notably covered by the Eagles, is downright beautiful, and "I Hope That I Don't Fall in Love with You" is probably as close to Jackson Browne as Waits ever got. (I mean that as a compliment.) This may not be the Waits who got famous, but it's still a great standalone work and proof that Waits didn't have to be banging on trash cans to write great songs.

Listen: "Ol' 55"

 

4. Mule Variations, 1999

Though Mule Variations isn't as adventurous as Real Gone or as taut as Bone Machine, it's a strong work that shows even when Waits takes his time in between albums, he never misses a beat. His beatboxing on "Big in Japan" prefigures Real Gone, and the monologue in "What's He Building in There?" proves he doesn't have to bellow to be scary. "Come On Up to the House" would be the by-now-requisite "ballad," but the lurching drums and withering harmonica solo by Charlie Musselwhite defy such easy categorization.

Listen: "Come On Up to the House"

 

3. Swordfishtrombones, 1983

Sort of a sister album to Rain Dogs, Swordfishtrombones suffers only from a lack of focus — three of its fifteen songs are instrumentals, and "Frank's Wild Years," "Johnsburg, Illinois," and "Trouble's Braids," feel more like sketches than actual songs. Spiked with brilliance as it is, the album still feels more like a warm up to Rain Dogs than a stand-alone masterpiece. Highlights include the stately "In the Neighborhood," the rollicking "Down, Down, Down," and the badass field holler, "16 Shells from a Thirty-Ought Six."

Listen: "16 Shells from a Thirty-Ought Six"

 

2. Bone Machine, 1992

Stark and driven where much of his '80s work is lush and meandering, Bone Machine is one of Waits' darkest albums, though it displays a certain gallows humor, notably on "Goin' Out West," with its twisted blues boasting: "I know karate, voodoo too — I'm gonna make myself available to you / I don't need no makeup, I got real scars." The album is relentlessly harrowing and bleak, and its echo-laden, stripped-down production is primal and unnerving. But there's tenderness here, too: "I Don't Wanna Grow Up" is an innocent, sing-songy chant plaintively rendered over a simple arrangement, while "Who Are You" and "That Feel" are two of Waits' most nakedly emotional songs.

Listen: "Goin' Out West"

 

1. Rain Dogs, 1985

Oft-cited as Waits' defining work, Rain Dogs is a beautiful summation of Waits' surreal take on nearly the entire history of American music (and some international flavor as well), from the hypnotic hillbilly drone of "Gun Street Girl" to the murky stomp of "Big Black Mariah" (one of several notable guest appearances by Keith Richards). It's impossible for me to pick a "best song" from this album, but I'm going to go with a more subdued pick: the haunting ballad "Time," which features some of Waits' most poetic lyrics.

Listen: "Time"

 

And for a much more in-depth (and I mean much more) look at the Waits canon, check out my Tom Waits playlist for Spotify.