26. Stan Rizzo
Showcase Episode: "Time & Life"
After starting out as just another macho office clod, Stan developed warmth and soul in proportion to his beard — definitely Mad Men's most successful experiment in facial hair. Jay R. Ferguson is masterful in the scene where Peggy tells him about giving her baby up for adoption — as he realizes where she's going, he listens with empathy and respect. It's the show's most optimistic sign that sexism isn't necessarily a life sentence. Love the groovy Moshe Dayan poster over his bed, too.