23. Alice Cooper
Showcase Episode: "The Mountain King"
It makes sense that Bert Cooper's bad-ass sister shares her name with a rock & roll god — "No More Mister Nice Guy" could be her theme song. Alice Cooper is the only one who gets away with wearing shoes in Bert's office ("My stockings cost more than your carpet") or calling him Bertram. She also used to be Roger Sterling's babysitter, which might be why she gives him so much shade about marrying a 20-year-old. ("You have your children to think of." Meee-yow!) She talks her brother into selling off his life's work — but as the other Alice Cooper would put it, if that don't suit you, that's a drag.