Who are the scariest dudes in rock and/or roll? The first one that popped into my head was Nick Cave. Not only does he look like the spawn of Dracula, but his music sometimes freaks me out too. According to our friends at Wikipedia, the Aussie and his band are, "renowned for its highly dark, challenging lyrics and violent sound." That's putting it nicely!
Nick Cave and the Bad Seeds - I'm Gonna Kill That Woman.mp3
Buy (MP3 only): Kicking Against the Pricks (1986)
Roky Erickson has made a career of being all psychedelic and freaked out. Many of his songs were influenced by horror movies. He played in Toronto last week with my favorite Canadian band, The Sadies, and I am irritated that I missed it.
Roky Erickson and the Aliens - Bloody Hammer.mp3
From: The Evil One (1981, out of print)
Buy: The Evil One (plus one) (2002 reissue with lots of bonus tracks)
I heard this song for the first time while driving from Calgary through the desolate Rocky Mountains to Banff, Alberta, and it scared the bejesus out of me!
Tom Waits - What's He Building?.mp3
Buy: Mule Variations (1999)
In my opinion, this is the creepiest song of all time. The narrator misses his dead girlfriend so much that he digs up her grave and climbs into her coffin just to be with her. Eeew!
Downliner Sect - I Want My Baby Back.mp3
From: Sect Sing Sick Songs (1965, out of print)
Buy: The Country Sect (2005)