DURING THE FIRST, formative decade of his career, when he was largely based in Los Angeles, Tom Waits mined a rich seam of the city's lowlife locations and noir associations. Right from the outset, Waits liked to mix the domestic with the mythic, turning his own quotidian details into something far darker and more emblematic. Waits's famed residency at the Tropicana Motor Hotel managed to combine both these impulses. “There is a kidney shaped swimming pool in the courtyard,” William Burroughs wrote in Rolling Stone in 1980. “On the patio are rusty metal tables, deck chairs, palms and banana trees: a rundown Raymond Chandler set from the 1950's. One expects to find a dead man floating in the pool one morning."

This pleasingly named, deeply unsanitary West Hollywood motel featured as the main location for Paul Morrissey's film Andy Warhol's Heat (1972) and was already renowned for its cool sleaze by the time Waits checked into his two-room apartment in 1976. There, half-buried under his stash of records, girlie mags and empties, Waits exhibited a semi-public enactment of his stage persona, a version of the Beat musician in tune with the poetry of the streets. The ungovernable state of his room became part of the legend. Barney Hoskyns, in his excellent biography, Lowside of The Road, quotes a friend of Waits's, who opened the fridge in search of a beer, and found only "a claw hammer, a small jar of artichoke hearts, an old parking ticket and a can of roof cement." It even sounds like a line from one of Waits's spoken-word poems of the time.

Waits had formed a small bohemian circle, which moved from the Tropicana to sober up over coffee at Duke's and spent their nights at the Troubadour. Waits's main sidekick and conspirator was Chuck E. Weiss, a good time guy originally from Denver who loved his drugs and tall tales. Made famous by Waits’s one-time girlfriend Rickie Lee Jones's serenade, Chuck E. also received a Waits tribute in the track “Jitterbug Boy” (from Small Change, 1976). The song showcases one of Waits's fondest early personas, that of the buttonholing boozer, bending your ear with ever more outlandish stories, and has the extended subtitle “Sharing a curbstone with Chuck E.Weiss, Robert Marchese, Paul Brody and the Mug and Artie.”

This is the high watermark of Waits's self-mythologizing Los Angeles legend, the time he deliberately set about living the life his songs described. In 1982 he told Dave Zimmer of Bam:

I really became a character in my own story. I'd go out at night, get drunk, fall asleep underneath a car. Come home with leaves in my hair, grease on the side of my face, stumble into the kitchen, bang my head on the piano and somehow chronicle my own demise and the parade of horribles that lived next door.

Out carousing with his boys all night, attracting female admirers who would camp out on the porch of his bungalow and wait for his early hours return, Tom Waits started to resemble "Tom Waits":

When I moved into that place it was nine dollars a night. But it became a stage, because I became associated with it. People came looking for me and calling for me in the middle of the night. I think I really wanted to kind of get lost in it all and so I did.

It wasn't just that Waits’s lush life had turned into a kind of prison. H...