31. Duck Phillips
Showcase Episode: "Three Sundays"
So many ups and downs for the Duck — most of them involving the bottle, as in the drunken rant that gets him dragged out by security at the Clio Awards. (Roger Sterling cracks, "I miss working with that guy.") His pivotal moment: at a secret meeting with the Brits, taking a sad look into his martini glass, right before he takes that fateful sip and makes his pitch to sell Sterling Cooper. Alas, he never could hold his liquor.