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10. Duck, Duck, Gross
Duck Phillips’ fall from grace wasn’t a pretty one. At one time he was a top dog at Sterling Cooper, but by season 4 he was a mess, begging Peggy to join him in a doomed-to-fail joint venture and drinking too much. Pickled and humiliated, he tries to exact revenge on his former nemesis Don by leaving an unpleasant ”present” in his office, but instead gets caught pants-down by Peggy in Roger’s office before getting into a tipsy reenactment of the Clay-Liston fight with Don. —Keith Staskiewicz
Image Credit: AMC
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