Wow Deimos, you opened a can of worms! ;) I was a comedy writer for about 5 years out of college and one of my partners is a freelance writer for Late Night with David Letterman and was a staff writer for the now defunct Chris Rock show on HBO (Chris Rock himself cancelled the series). Me? I took the computer route. So here I sit at my relatively boring multimedia developer job, waiting for a sight gag to erupt.