I stopped watching the first season of Mad Men before it ended, and keep meaning to pick it up again but haven't. But Michael Brendan Dougherty's take on the show as a whole dovetails with my own initial impression - namely, that it wears its condescension toward its era and characters on its sleeve, inviting the viewer to enjoy the guilty pleasures of the early 1960s secondhand, while looking down, with "how far we've come" smugness, on the people who actually enjoyed them in the flesh. In its early going, Mad Men seemed to be aiming for the same trick David Chase pulled off in The Sopranos - depicting a corrupt lifestyle as simultaneously repellent and attractive, and then gradually (very gradually, in Chase's case) implicating the audience in the moral turpitude it was eagerly awaiting every Sunday night. (See Emily Nussbaum's brilliant Sopranos exegesis for more on this theme.) But Mad Men suffered from two big problems, at least in the episodes I watched: First, the show lacked The Sopranos' playfulness, its understanding that sin wouldn't be alluring if it didn't seem so damn fun. (As Dougherty puts it, "the writers give [Don] Draper the desperate, needy conscience of an addict, without ever showing him enjoying the high.") Second, its creator and writers didn't seem to realize that early-sixties admen, whatever their bigotries and vices, weren't quite the moral equivalent of murderous gangsters, and thus that a dramatic approach that worked in Chase's mob story would often end up feeling strained and portentous when the subject matter wasn't murder, rape and drug dealing, but booze and adultery and ad copy.
All of that said, it had obvious charms - Dougherty obviously likes the show in spite of itself, and of course everyone else loves it - and hopefully I'll pick it up again soon and discover that I'm being somewhat unfair in my criticisms.