11. Blue Valentine, 1978

Blue Valentine dropped the string section (with the exception of Waits' great take on West Side Story's "Somewhere") and added the shimmering sounds of electric piano to Waits' rapidly changing voice. The result is a bluesier album, but one that doesn't sacrifice the emotions of its predecessors. "Red Shoes by the Drugstore" manages to be both driving and atmospheric, by virtue of the electric piano and relentless drums. "Christmas Card from a Hooker in Minneapolis," adapted from the Charles Bukowski poem "Charlie, I'm Pregnant," is a crushing character portrait with one of the all-time greatest lyrical twists at its conclusion.

Listen: "Christmas Card from a Hooker in Minneapolis"

10. Alice, 2002

Alice is a collaboration by Waits, his wife Kathleen Brennan, and playwright Robert Wilson, about Alice Liddell, who inspired Lewis Carroll's Alice in Wonderland books. The album finds Waits at his most subdued and almost off-puttingly somber. Alice is almost a period piece: the violins are all Stroh violins (which are are outfitted with small tin horns to amplify their sound), and the whole thing sounds like a lost cabaret work.

Listen: "Alice"

9. Bad As Me, 2011

Waits' most recent songs are also, surprisingly, some of his most concise. Where some artists grow less focused as they age, Waits has sharpened his vision, cut his run times, and made a lean, driven album. The album's opener, "Chicago," is a horn-driven uptempo rave, and "Bad As Me" finds Waits cycling through his voices over an off-kilter beat. "Hell Broke Luce" is a real show stopper, a positively apocalyptic vision of war from the front lines, with Waits bellowing "How is it the only ones responsible for making this mess / got their sorry asses stapled to a goddamned desk?"

Listen: "Bad As Me"

8. Small Change, 1976

Small Change shows Waits in transition. His voice is newly rough, but he hasn't yet shed the trappings of his early work: the string section is still present and mawkish sentimentality is still at the fore. Some of it is grating: "Pasties and a G-String" seems almost like a mocking caricature of his blues and jazz idols, and on "Jitterbug Boy," he slurs his words nearly past the point of comprehension. That said, "Step Right Up" is one of the most entertaining songs he's ever cut, and features the indelible line "The large print giveth and the small print taketh away."

Listen: "Step Right Up"

7. Franks Wild Years, 1987

Though Franks Wild Years is uneven and cluttered, it's still graced with some of Waits' best songs. "Hang on St. Christopher" barrels along with manic glee, and "Straight to the Top" is a demented tale of aspiration presented both in "Rhumba" and "Vegas" form ("Rhumba" wins). "Temptation" displays the full capabilities of Waits' ravaged but surprisingly agile falsetto. Finally, "Innocent When You Dream" caps off the proceedings as a wistful retrospective; the "78" version recreates the song as though heard through a hole in a Lost Generation Paris cafe wall.

Listen: "Innocent When You Dream (78)"