43. The Madam
Showcase Episode: "Signal 30"
Mad Men has to hold some kind of record for one-scene sensations — characters who only need a moment or two onscreen to burn themselves onto your brain forever. Think of Roger Sterling's divorce lawyer ("I have a list of conditions and an alimony that could support Rita Hayworth"), the Belle Jolie lipstick salesman, Pete Campbell's dad, the Clio Awards MC ("Gentlemen, let's pace ourselves"), Achilles the janitor or Duck Phillips' dog. But few characters make a bigger impression in less time than the whorehouse madam (veteran character actress Eve Gordon) who notices Don Draper alone at the bar. They recognize each other as kindred spirits, or at least people who know way too much about whorehouses. "So expert, what do you think? Should I get a TV in here?" A moment of bonding — and then back to business.
(Note: In case you're keeping score of Mad Men's endless JFK obsessions, Eve Gordon played Marilyn Monroe in the 1991 miniseries about Jackie Kennedy. Happy birthday, Mr. President!)