“…this was our favorite episode of the season: sharply written, beautifully acted, and almost overwhelming. Thematically, you have to ask: Why does Don have such a wild, gothic backstory? Here’s one partial theory: Mad Men has always been obsessed with mirroring and self-perception, and maybe self-delusion. Almost every single character — Betty, Sal, Pete, Joan, Roger, Peggy — is struggling to embody some idealized self-image, and always falling short.
Don is at the center of this story because he’s the only one who discards his old self and constructs an entirely new one from scratch. “You’re a very gifted storyteller,” Betty tells him. He’s the living promise of advertising, which always says that if you buy this (or that, or another thing), you can be different. Almost all advertising (and especially advertising of this era) promises aspirational change, and whether the result is a happier you, a sexier you — or a more glamorous you, a more powerful you — it’s a different you in the end.
… “And who are you supposed to be?” the man with the candy asks Don, when his children show up as a hobo and a gypsy. It’s a beautiful line — the best symbolic capper to any episode this season — not because it’s cute, but because it gets at the idea that Don, having aped so many bits of this and that (a little Tyrone Power, a little Roger Sterling, a little David Ogilvy, and much more), probably can’t answer the question at all. He’s his most important account, and he’s about to lose it.”
Mad Men: The Masked Ball
New York Magazine
ED NOTE: A lot of thoughtful analysis to be found on Episode 11, Season 3: The Gypsy and the Hobo” of Mad Men. Considered by all to be the best of the season. Deservedly so. This review, in my opinion, is one of the most insightful.