Richard Thompson singing “I feel so good, I’m gonna break somebody’s heart tonight…” is a great portrait of a jerk.
Stagger Lee, on the other hand, is more a straight-up murderer than an insensitive twit.
Frank Zappa…take your pick. The emcee of “Wet T-Shirt Nite” comes to mind. (“Yes, that water is cold, kind of feels like an ice pick to the forehead. And now the ice pick to the forehead!”)