2. Roger Sterling
Showcase Episode: "Shut The Door, Have A Seat"
Has anyone in TV history made a deadlier wisecrack delivery machine? Compared to Roger Sterling, Johnny Carson was some tongue-tied amateur. His toast at his daughter's wedding — the day after the JFK assassination — remains a model for how to bullshit your way through a disaster, as does his whole life. John Slattery brings the "Have a drink, it'll make me look younger" pain; under all his bravado, he's a salesman with nothing to sell. But Roger's the Proposition Joe of Mad Men: When he steps into a scene, you can see the others light up. Everybody's best scenes are their Roger scenes. So let's all raise a parting glass to this man. It'll make him look younger.