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.