11. Freddy Rumsen
Showcase Episode: "Six Months Leave"
Nobody better exemplifies how Mad Men goes for the long bomb, character-wise. Freddy Rumsen starts out a drunken mess with a weak bladder but a heart of gold — if he hadn't overheard Peggy's "basket of kisses" comment and groomed her as a copywriter, she'd still be stuck in the secretarial pool. Over the years, he evolves into a different guy: sober, thoughtful, doling out Yoda-like wisdom. ("Do the work, Don!") Played by Joel Murray (Bill's brother), Freddy is a lovable slob every step of the way.