Cast a novel, play, musical, television show or movie with the characters of Mad Men. It can be from the era of Mad Men, something from decades before, or something more modern. I’m going to present a partial list from Bewitched as an example:
Gender-bending is allowed, if you think it works personality wise. While a version of this may have been before, enough new characters have been added to the series to merit doing it again. The point is to be creative and have fun.