17. Anna Draper
Showcase Episode: "The Good News"
When the original Don Draper got blown up in Korea, leaving the young Dick Whitman to steal his dogtags and identity, he left a wife behind. After she catches up with Dick, they begin one of Mad Men's most touching and endearing friendships...especially when he paints her living room in his boxer shorts. True, their whole relationship is founded on another one of his lies. (He says her husband got killed in action, leaving out the detail that Dick Whitman was the one who blew him up.) But Anna knows the man and his secrets better than anyone.