14. Pete Campbell
Showcase Episode: "New Amsterdam"
From the start, one of the lowest critters in the Mad Men universe — but as soon as we meet his horrible old-money WASP family, we understand. Nobody ever taught Pete how to be a human being, and he learns by random baby steps, although too late to save his marriage. He remains an unimpeachable yeller of punchlines, from "Marriage is a racket" to "Not great, Bob!"