This one takes a few minutes to really get going but, wow, once it does it offers one home-run scene after another. The action mostly takes place on one Saturday, in a classic “Mad Men” structure where the scenes bounce between several different groups. The main thread has Roger and Jane hosting a Derby party at their country club, and it offers us introductions to two important characters: Conrad Hilton and Henry Francis. Elsewhere, Joan and Greg host a party for Greg’s medical colleagues; Peggy, Kinsey, and Smitty are working at the office and end up getting high; and Sally steals $5 from her grandfather back at the Draper house. Matthew Weiner has a tendency to lay his themes on a little thick, but what I love about “My Old Kentucky Home” is how inscrutable it is. It also offers one of the best closing shots in the show’s history, with Don and Betty kissing in the moonlight. This is the kind of episode that you can’t envision any other television show being capable of creating.
Best Scene: In one of the more shocking scenes in “Mad Men” history, Roger serenades Jane in blackface during the party. Looking to escape the fiasco, Don retreats to a bar inside where he meets a man that will change the course of this season: Conrad Hilton. Their conversation is one of the best moments of the entire series.
Best Line: Roger to Don: “You know, my mother was right. It’s a mistake to be conspicuously happy—some people don’t like it.” Don: “No one thinks you’re happy. They think you’re foolish.” Roger: “You know, that’s the great thing about a place like this. You can come here and be happy, and you get to choose your guests.”