Many know Anna Osceola as Jon Hamm's wife, and while the pair did meet on the Mad Men set, many are surprised to learn who Osceola played. The acclaimed AMC series centers around Hamm's Don Draper, an advertising executive in 1960s New York who's a chronic womanizer. Don is repeatedly unfaithful throughout both of his marriages, finding sexual conquests at the office, swanky Manhattan cocktail bars, and even California, a place near and dear to Don's heart that he visits frequently throughout the show.

It's California where Don finds himself in the series finale, and the Mad Men ending sees him the lowest he's ever been. He's all alone, having divorced Megan (Jessica Par), and has recently learned that his other ex-wife, Betty (January Jones) has terminal lung cancer. Despite her prognosis, Betty doesn't want their children to live with Don. Full of regret, Don turns to the...