When we last saw Don Draper, he was in bed with a woman he barely knew. And while in many ways that might seem like a typical day at the office for this guy, this woman was wearing his engagement ring. The same diamond ring that Lt. Don Draper put on Anna's finger all those years ago, and the ring that represents yet another one of the former Dick Whitman's attempts to make a fresh start. That's what makes Don Draper such a quintessential American fool, and helps explain our obsession with him. Every American wants a clean slate, but nobody wants to lose what they've got.
Which is why every American's a sucker for the next scam artist who promises them a new tomorrow – and Don Draper, as the greatest of scam artists, the one who never fails to seduce the rubes, is also the biggest sucker of them all. As Peggy said to Joan, shaking her head in disbelief, "A pretty face comes along and everything goes out the window." Don Draper knows how that works – he's a pretty face himself, and he's built a career hustling in the dirty world of American dreams. But nobody falls for a con harder than a con man.
Mad Men is the most astonishing, revelatory drama of our time, in any medium or format, and it's coming off two of the most sensational seasons in TV history. Judging by the premiere episode, Season Five is on the same level. In other words, we're still in the prime of our Mad Men moment. And without getting into any of the details of what's happened or how long it's been since we last saw these characters, suffice to say, it's correct to assume they are as glamorously fucked as ever. This is still a world where people pick up babies while clenching lit cigarettes between their teeth. It's a world where pot is "tea," and business meetings mean martinis.
Season Four ended with the most shocking plot twist Mad Men has ever seen: Don impulsively gives that engagement ring to Megan, a secretary he's basically just met, after a trip to (where else?) Disneyland. As Mad Men viewers, we haven't spent much time with Megan, either. All we really knew was that she was a sultry young hipster from Montreal, which can only mean she's banged Leonard Cohen and inspired him to write at least one miserable love ballad. (My money's on "Famous Blue Raincoat.")
Many fans were horrified to see Don act like a starry-eyed sucker, instead of the cool customer we need him to be. It turns out this guy believes in Hollywood happy endings. He's not satisfied to sell the American dream – he wants to believe. And if even Don Draper falls for his own promises, what hope is there for the rest of us?
One of the reasons Mad Men inspires such passion is that it's always a pleasure to knock a few back with these characters. We know too much to trust them, but they're likable – as any long-con grifter needs to be. However, there's a new anxiety that lurks right below the bravado. Their world is changing, and some of the sharks at Sterling Cooper Draper Pryce are adjusting more smoothly than others. Yet for all of them, survival means turning on the surface charm even when they're falling apart inside.
Early in the new season, a jazz band tootles away at the 1965 hit "The 'In' Crowd," and it's a stunningly understated bit of music commentary. Everyone on Mad Men wants to be in with the in crowd. And they're desperate to imitate anyone who can show them how it's done. Don Draper wins people over by coming on like the innest of the in crowd – he's the guy who knows. On Mad Men, that's part of the Sixties scene – this is a moment in American history where everybody wants some role in the Don Draper story. But the man is a masquerade, and that's the reason Mad Men keeps getting more fascinating. The secret of the in crowd is that there's nothing in there – except more mystery.
This story is from the March 29th, 2012 issue of Rolling Stone.