29. Kurt Smith
Showcase Episode: "The Jet Set"
When the Sterling Cooper bosses decide to dip a toe in the Sixties youth movement, they hire the duo or Kurt and Smitty, who look like the world's first Simon & Garfunkel cover band. Smitty reads Don the original Port Huron Statement (not the compromised second draft), while German designer Kurt casually comes out as the first openly gay dude anyone's ever met. ("I make love with the men, not the women.") Oh, the sad look on Sal's face. In a sublimely moving scene, Kurt meets Peggy for a Bob Dylan concert, then blows off the show to stay home ("You are drinking sad") and change her life with her first mod haircut.