48. Harry Crane
Showcase Episode: "The Wheel"
A creepier, sweatier Pete Campbell, with no redeeming qualities, except maybe his touching fondness for White Castle burgers. Some of us have never forgiven him for ratting out Sal and getting him fired. Harry Crane was a likeable loser in the early seasons, always inept at sucking up to big shots — as in his painful attempt to discuss modern art with Bert Cooper. He finally gets some respect when he meets his soul mate Jim Cutler, who tells him, "You have stiff competition, but I believe you to be the most dishonest man I have ever worked with." At Sterling Cooper, that's high praise.