When I was volunteering at a con's art gallery years ago, making sure nobody messes with the artists' works. I happened to be looking at a Little Wooden Boy from show The Tick. Somebody comes and says he know the artist who made that and we chat a bit and he mentions that artist was willing to do anything for a commission. No request was too absurd or ridiculous as long they had the money.
He mentioned the weirdest and degenerate request this artist did was some dude wanted art of Sonic the Hedgehog having sex with a supermodel (I can't remember the name). The man who wanted this commission, requested every artist he knew but all of them rejected it except one. The artist who did it didn't care, it was money somebody was willing to pay for and it got done.