His debut, a set of tender late-night ballads and jazzy piano tunes. The voice is still soft here, years before the gravel arrived.
A romantic ode to diners, bars and the American night, sung in a warm, boozy croon. The songwriting takes a big step forward.
The barfly persona in full bloom: whiskey-soaked jazz, spoken-word tales and the raspy voice fans came to love. His breakthrough of the seventies.
Cinematic and noirish, full of strings and smoky atmosphere, including a duet with Bette Midler. The lounge-jazz world at its most filmic.
A grittier, bluesier turn, trading piano for electric guitar on tales of losers and lovers. The romance sours into something darker.
The last of the early jazz-blues records, split between raw growling rockers and aching ballads. A hinge before the great reinvention.
The great reinvention: clanging percussion, marimba and pump organ replace the lounge polish. Junkyard sounds and theatrical vision take over.
A sprawling masterpiece of urban misfits, blending blues, tango, marimba and Marc Ribot's spiky guitar. Widely seen as his finest hour.
Music from his stage play, a cabaret of accordion, lounge organ and broken-down carnival tunes. The most theatrical record of the trilogy.
A stark, apocalyptic record full of bones, dirt and mortality, recorded in a concrete room for maximum rattle. It won a Grammy.
Songs from the theatre piece with Robert Wilson and William S. Burroughs, a haunted German-cabaret carnival. Waits at his most avant-garde.
A rich comeback mixing junkyard blues with tender ballads, blending his two sides. It won the Grammy for Best Contemporary Folk Album.
One of two albums released the same day, drawn from a stage adaptation of Woyzeck. Bitter, earthy songs about greed and human frailty.
Its twin release, based on a play about Lewis Carroll and Alice Liddell. Dreamy, submerged ballads, far gentler than Blood Money.
Built on beatboxing, turntables and no piano at all, his most rhythmic and abrasive record. Raw, political and relentless.
A tight, punchy set that gathers every strand of his career into short, sharp songs. His last studio album to date.