A buddy of mine who ran his own studio once asked me to do an illustration for a strange request that a customer had. I had done a number of custom pieces, and some of them were pretty damn weird.
This one, though...
The guy essentially wanted a portrait of a 60's era William Shatner "deep in thought." He also wanted a dream bubble coming out of Shatner's head, and inside that dream bubble he wanted the exact same portrait of William Shatner with a mustache.
Essentially William Shatner dreaming about William Shatner with a mustache. The dude wanted this engraved on his flesh. I was in awe of how beautifully stupid it was.
Being that portraiture wasn't my strong point, I gave it to someone else. Last I had heard, the guy actually went through with it.