I'd guess I'm right about half the time, and when I'm wrong it is almost always a very happy accident, so I never record vocals without trying several microphones. I tend to narrow the field to start, but I've been know to try everything in my locker on occasion.
That said... if I were recording Mr. Waits I'd start with an older AKG C-414, a Blue Baby Bottle, a Shure KSM-32, and a Neuman TLM-193, and I'd put my money on the TLM-193. But I've been surprised often enough that I would still try all four!!