Over and over again, "Waterloo" tried to define Don Draper. He is "an old, bad boyfriend," the kind of guy "a teenage anthropologist would marry." He is "a bully and a drunk." He is a "football player in a suit." He is "a sensitive piece of horseflesh.” He is "a pain in the ass." All these definitions, and none fit.
You want to know what that musical number was about? The only honest answer is … we don't know yet. When Mad Men comes back in a year, we'll learn if Don had a stroke, if he's in the throes of a psychotic breakdown, or if AMC finally pulled the trigger on that Walking Dead crossover episode. (For the record: Duck Phillips would thrive in a zombie apocalypse. He killed 17 men at Okinawa.) Twelve months is a long time to wait, though, so I'll propose a theory.
As I see it, the song reveals a lot about Don's identity and state of mind. Sure, the McCann merger will make him rich—but as he told Ted, he'll still have to work. (And let's not forget how he called the place a "sausage factory.") His new boss is a schemer, not a leader. He still hasn't controlled his alcohol problem. He just lost his second wife. He is about to become a rich, sad, miserable man. "The Best Things in Life Are Free" reminds him that, well, the best things in life are free—and he doesn't have any of them. We know that Don has hallucinated before, and this time, he seems to realize that it's all in his head. He recognizes that he's losing his mind. We just don't know how he'll finally snap.
Fetters: “He just lost his second wife.” So we’re pretty sure about that this time, right?
There have been a few other times this season when we thought we were seeing the end of Don and Megan’s marriage—most memorably, the fight that ensued when Don made a surprise visit to California. Megan even said to Don, “This is the way it ends.” And yet they’ve gone on as though it never happened, as though they’re still trying to make it work. I had started to get the feeling that show was crying wolf (or crying divorce, as it were) with Megan and Don. But I do think, this time, that this is actually how it ends—limply and passively, with a very telling awkward silence during an otherwise routine phone call.
That phone conversation, it bears mentioning, is a lovely, thoughtful piece of writing. Megan’s momentary hesitation as to whether she wants her husband to move to California tells both us and Don everything we need to know. With just one or two seconds of silence, their conversation turns from hopeful to resigned, and their marriage seems to have finally dissolved.
(Well, maybe. Again, you really never know with these two.)
Another nice touch: I could watch that slow-motion sequence at the start of the Burger Chef pitch meeting for days. Soundlessly, accompanied by only a low, ominous hum, the camera pans from one middle-aged man in a suit to the next, all the way down the table—every one of them ignoring Peggy’s presence. Simply put, it’s a gorgeous reminder of what Peggy’s story has been throughout this series: the struggle to succeed in a world that thinks she doesn’t belong in it. Prefacing the pitch meeting with that sequence from her perspective made the successful Burger Chef pitch—which may very well be Peggy’s “Carousel” moment—all the more rewarding.