18. Paul Kinsey
Showcase Episode: "Nixon vs. Kennedy"
The office hepcat: a young Orson Welles type smoking his pipe, growing his beard, writing plays and throwing parties where he busts out astoundingly obscure R&B sides. (George McGregor and the Bronzettes' "Temptation Is Hard To Fight" — damn! Easily the best song I discovered via Mad Men. Thanks, DJ Death Is My Client!) Paul has an intriguing romantic history with Joan. But he tragically gets left out of the new-model Sterling Cooper and things go downhill for him, until he winds up a Hare Krishna. Hey, it's better than what happened to the real Orson Welles.