Songs that have always oozed coolness to me - but I'm a huge geek, so I don't know how cool regular people would consider 'em. I feel like cool mofo if they're playing in my car, though.
Violent Femmes - Kiss Off
Monster Magnet - Powertrip
Gorillaz - Clint Eastwood
Weezer - Say It Ain't So
Red Hot Chili Peppers - Under the Bridge
White Stripes - Dead Leaves and the Dirty Ground
Ben Folds - Rockin' The Suburbs