3. Willie T. Stokes - Bad Santa
It's impressive how bad at his job Willie T. Stokes is given that he only needs to spend a few times a year in December doing it. The guy plays a mall Santa, and once the mall closes, schemes to steal money from the mall vault with his elf buddy Marcus (Tony Cox) on Christmas Eve, securing him a big enough haul for the whole year. He then repeats the same shtick at another mall the next year, and this has so far kept him pretty sweet, even as his alcoholism and sexual addiction begin to take hold. For a man who should do his best to keep a low profile, Willie makes a concerted effort to draw attention to himself, being drunk on duty and hooking up with unsavoury mall patrons. He has probably the easiest job of anyone on this list; he just has to turn up a few times a year and then enjoy himself. But he can't even do that properly.