20. Woman on the Train
Showcase Episode: "Nixon vs. Kennedy"
She's only in one scene — but what a scene. It's the moment that truly turns Dick Whitman into Don Draper; just back from Korea, in his new identity, he meets a woman on a train, probably the first person who ever spoke a kind word to him. She might be a war widow herself (she's wearing black gloves) but she gives a heartbreaking little speech to Don ("You've got your whole life ahead of you — forget that boy in the box") and flirtatiously suggests, "Let me buy a soldier a drink?" All these years later, Don Draper is still that scared soldier, looking for that woman.