Originally Posted by The Monkey

Four albums that I think are the best way to show most of Waits' sides are:

Closing Time - His debut album. Rather jazzy, with a few folk influences. He tries to sing "normally" on this album, which is rather interesting. Rather warm and calm album with beautiful lyrics mainly about (lost) love. Goes best with red wine.

Small Change - His drunkest and funniest album. Tom sounds like a hobo somebody dragged in from the street and placed in front a piano.
The lyrics are hilarious and deal with alcohol and cold women. Goes best with beer.

Rain Dogs - His most acclaimed album, and rightly so. Brilliant production throughout, and Tom's song-writing is as top-notch as ever. Virtually every instrument under the sun is featured, and the lyrics are usually abstract and about random suspicious characters of the American city (midgets, prostitutes etc.). Goes best with whisky.

Bone Machine - One of his darkest albums; Tom's voice reaches its lowest register. Deals with death and betrayal. Some songs go beyond being dark and become outright scary. Goes best with weed (if you're sober before and in the right mood!)