50 Best 'Mad Men' Characters

From one-off cameos to Sterling-Cooper's core players, we're ranking the show's most memorable characters

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Jane Siegel Sterling
Carin Baer/AMC39/50

39. Jane Siegel Sterling

Showcase Episode: "Far Away Places"
Roger marrying a 20-year-old secretary — how did that go wrong? At first Jane sets her sights on Don, but she settles for Roger, who admittedly brings his A-game. ("Where did you get that sweater? I want to make sure my daughter never buys it.") Jane is a self-styled poet and clairvoyant who offers a poignant epitaph for JFK: "He was so handsome and now I'll never get to vote for him!" She also brings Roger along for her fateful acid trip, which doesn't go as planned.

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