If you've never heard of Tom Waits, he is a singer/songwriter who has been around since the 1970s. I have only recently discovered him within the last 3 or 4 months, but he's great.
Be forewarned: his voice is not for the faint of heart. He is essentially a grizzled old man who sounds as though he's making fun of another more grizzled old man while singing. But he's just really cool. I've got about 5 or 6 of his albums (these are the benefits of sharing music with middle-age hipsters at work), and my favorite is his latest, "Orphans: Brawlers, Bawlers, and Bastards" which is a collection of B-sides and greatest hits separated into relatively up-tempo bar fight music ("Brawlers"), ballads ("Bawlers") and I guess just random studio recordings ("Bastards"). My favorite by far is the "Bawlers" disc, because it's odd and yet strangely comforting to listen to an old wino sing about broken hearts and empty bottles. I picture Barney Gumble singing for brandy in that Simpsons with Sherry Bobbins. If you can get past his voice (which I now really like), he's a great songwriter. It's mostly blues and acoustic guitar, piano, and some horn, maybe an oboe? What's the jazz horn that isn't a trumpet or saxaphone? Whatever it is, this is perfect whiskey music and I could definitely see him playing in a bar with 3 people in it at 2AM. This is pretty much his material:
"Give a man gin,
give a man cards,
give him an inch,
and he takes a yard."
According to Wikipedia, his voice sounds "like it was soaked in a vat of bourbon, left hanging in the smokehouse for a few months and then taken outside and run over with a car."
And if you listen to Toucher and Rich on WBCN, he could be mistaken for the immortal Chili Guy. He's that drunk, and he's that grizzled. Tom Waits is The Man.
That pretty much sums it up. He's made his way into my regular rotation, particularly on these dreary winter days. He's worth at least couple of iTunes purchases.