Thanks to costume designer Janie Bryant , Hamm's '60s ad man single-handedly revived an interest in the classic two-button suit.

Since the very beginning of Mad Men, Don Draper has seemed doomed. From the show’s opening-credit sequence, with a silhouetted suit falling helplessly from the Madison Avenue skyline, to this year’s season premiere, which featured Don delving into a copy of Dante’s Inferno, the future always seemed bleak for our dapper anti-hero.

Oblivious to the fact that he’s always on the wrong side of history, Don began to wither. What seemed cool about him in the beginning — his afternoon drinks and serial womanizing — has devolved to pathetic.

So where will it end? And more importantly, when? Will the year be 1969 when Mad Men returns for its seventh and final season? Or 1970? 1973…? Or might Matthew Weiner throw a curve and leap into the future — say 1980 — before flashing-back to the beginning of the previous decade.

Let’s discuss…

When we first met Don Draper in season 1, it was March 1960, perhaps the high-water mark of the American Dream after World War II and nearly a decade of Eisenhower prosperity, with the youthful optimism of Kennedy’s Camelot on the horizon. The center was holding. There was order. Life made sense (at least for upper middle-class white men). The story of Don Draper — and to a lesser extent Roger Sterling and the other men at the ad agency — has been the breakdown in society during one of the country’s most turbulent decades: racial strife, feminism, Vietnam, political assassinations, etc.

Weiner has only once jumped more than a year between Mad Men seasons — season 2 began in February 1962, 15 months after season 1 left off — and the average time-jump is about nine months. So it’s a safe bet that the final season will pick up sometime in 1969 after season 6 left us in front of Don’s childhood abode around Thanksgiving 1968. That makes some logical and symmetrical sense, too, since it wraps up the story of the decade quite neatly.

But up until last week’s season finale, I thought Weiner, Don, and Mad Men were steering towards a very different end. Don’s downward spiral accelerated every episode, and to me, it all pointed towards Watergate — the ultimate figurative and literal corruption of the country’s soul. There was even a recent episode where a drunken and depressed Don watched a bland Nixon-for-President commercial, and I wondered if the light would go on in Don’s head saying “Hey, I can carve a better winning message for my pal, Dick, than this amateurish crap!”

Remember, Sterling Cooper was a pro-Nixon company from the beginning, doing some pro-bono work for his campaign back in 1960. Maybe Don Draper would become Nixon’s new media consultant — the guy who remade the candidate’s Tricky Dick image and got him on cool shows like Rowan & Martin’s Laugh-In, the guy who might have made a hipper campaign ad, like this:

(Actually, there’s no way Don Draper would have signed off on this commercial.)

But I loved the idea that Don might become some romantic version of Roger Ailes, Fox News’ combative and controversial news genius. Ailes actually worked in television in the 1960s until a chance encounter with Nixon in the wings of The Mike Douglas Show propelled him into Nixon’s orbit and he helped tailor the candidate’s new persona. Don Draper as one of All the President’s Men? I loved the possibility of seeing Don’s personal life parallel and eventually intertwine with the country’s fortunes as both sank into the morass.

Don might have looked and moved more like Kennedy than Nixon, but there’s always been something connecting Don to Nixon, including their real first names and backgrounds. Dick Nixon of Whittier, Calif., wasn’t the bastard son of a prostitute, like Dick Whitman, but he grew up extremely poor in a devout Quaker household and spent his life trying to fit in with the high and mighty. No wonder Don said in last week’s finale: “I’m doing fine, Nixon is president, everything is back just the way Jesus wants it to be.”

But tying Don and Nixon’s fate together would require a giant, unprecedented three- or four-year leap into the future for season 7. And last week’s season finale seemed to show Don as he figuratively hit the pavement. He hit rock bottom. He told the truth about his horrible, twisted youth. He went home and showed his children where he grew up. There was a sliver of hope, of the potential for redemption. Don might still struggle in season 7, but he’s stopped his freefall, hasn’t he?

“A lot of the goal of the season was to drive people towards some sense of reconciliation,” Weiner said in the AMC video below. “That someone like Don would go through hell into a place where he would at least start to grow. The whole season is working up to this moment of Don taking a look in the mirror.”

After the horrible year of 1968, 1969 was a brighter day. Sure, there were echoes of the previous year’s tragedies — Vietnam continued to rage, for one — but there were also reasons to be optimistic. In July 1969, Neil Armstrong became the first man to walk on the moon; in August, the music world convened at Woodstock; and in October, the Miracle New York Mets won the World Series. There were also the Stonewall riots in June that helped spark the gay-rights movement. (Bring back Sal Romano!) On the darker side of things, there’s also the August 1969 Manson murders to deal with — though Weiner has said they are not necessarily on his docket despite the t-shirt that launched a thousand Megan Draper theories.

What makes 1969 even more likely as a final resting place for Mad Men are remarks that Weiner made two years ago when asked the how-will-it-end? question for the millionth time.

Weiner is referencing Abbey Road — the Beatle’s last recorded album, which was released in October 1969 — as an example of the best last act of creative collaborative brilliance, but there might even be something there in the content. “And in the end, the love you take is equal to the love you make,” goes the song, “The End,” the last song the quartet ever recorded. It’s a melancholy sentiment, one that could be both a told-you-so eulogy for a soulless Don, or an aspiration for a new beginning.

To be clear, I don’t think Don is out of the woods. As Weiner said in the AMC video, “I don’t think that he’s suddenly changed.” Season 7 is not going to be a victory lap for Don. Death, which has loomed over every season, will likely veer ever closer as the show reaches its end. But who, and how, and when? Will Pete finally succumb to Chekhov’s Gun theory? (“One must not put a loaded rifle on the stage if no one is thinking of firing it.”) Is Megan Draper in real danger all alone in Charlie Manson’s Hollywood in 1969? Will rebellious Sally be at Woodstock — or worse, Altamont? Will the “trip” Don took at the Hollywood party turn out to be his ultimate fate: Megan pregnant and him floating lifelessly in a swimming pool.

Weiner says he expects to begin writing the final season next month, so perhaps he still doesn’t have the precise setting and year for the show’s swan song. But it already feels like the summer of ’69.

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Thanks to costume designer Janie Bryant , Hamm's '60s ad man single-handedly revived an interest in the classic two-button suit.
Mad Men

Jon Hamm stars as Don Draper in the Emmy-winning ’60s-set drama

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