Digitaljukebox started a great thread called "songs everyone should hear at least once."
Here is my entry:
Bruce Springsteen: "Thunder Road"
The greatest rock & roll song ever. It touches on so many universal themes, I could't possibly name them all: Love, nostalgia, dreams that never came true, growing older and on and on.
Warren Zevon: "Roland The Headless Thompson Gunner"
A great story-song with all the elements of a film noir classic: love, violence, betrayal and a boatload of dark humor.
Chris Knight: "Down The River"
My nominee for the greatest story-song ever written, it is the tale of a man seeking vengeance for the death of his brother.
Drive by Truckers: "When The Pin Hits The Shell"
In this song, the narrator tries to cope with the suicide of a friend. It's not a very sympathetic song; while it does acknowledge some of the reasons a person may feel like ending it all, it also takes an uncompromising look at the damage done to those left behind.
Delbert McClinton: "When Rita Leaves"
Simply the best break-up song ever written. The lyrics are powerfully evocative and visual, so that you can picture the entire scenario in your head while listening. Delbert has a great voice, too, which makes this song even more powerful.