House of Dioxin

Driving home the other day, my iPod randomed up "Mack the Knife." At some point I realized that, hey, this is not (insert any of the many versions of the song I'm familiar with). Turns out it was Bing Crosby, which surprised me as he's not someone I'd think of as likely to sing "Mack the Knife." Even granting that most singers are covering the Bobby Darin version and not the Kurt Weill original, it's still a fairly dark song. And Crosby as a performer does not have much of a dark side. Okay, he's not as squeeky clean as Doris Day. On the other hand, in High Society he does manage to make most of C. K. Dexter Haven's thoughtlessly cruel bastard side just disappear. And yes, I'm aware that Crosby in real life™ apparently was quite a bastard. But that didn't come across in his performances which was why I was so weirded out hearing him sing a jolly little ditty about a serial killer. I should point out that, conceptual weirdness aside, Bing does a great job with the song. It's from a 50s record called Bing with a Beat and it's got a big, brassy, sorta Dixieland sound to it.
After that, I amused myself trying to think of the worst possible fit between a singer (within the Great American Songbook/Divaville Lounge genre) and "Mack the Knife." Sarah's suggestion of Doris Day is a definite winner. The one I came up with was Chet Baker.