Here's one I have to link to. Oddee has 15 Creepiest Old Album Covers. Now, the gospel quartet album doesn't look all that creepy to me. I first started learning music from guys who looked pretty much like that, and let's face it, a whole lot of people looked like that in 50s and 60s.
But then there's...
I'll have to give 'em that one. Quite creepy. I found several of the persons/groups shown listed at Wikipedia. Rae Bourbon is not one of them. But if you G00gl3 him...uh, her, or...whatever...you'll find plenty.
I know you must be thinking, ye gads! what did he do, go to Juarez, Mexico for the operation?! Well, yes, actually. He did.