The Bottom of the Glass: Legacy and the Last Season of ‘Mad Men’

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The first time we saw Don Draper, in the pilot episode of Mad Men, it was from behind: a stark silhouette, soon to be made famous across billboards, buses, and, eventually, benches. Moving through heavy, smoke-filled air, the camera swung around to reveal the man in full: immaculate, lacquered hair, a burning cigarette in his hand. Gray suit, white shirt, striped tie.

The first time we see Don Draper in “Severance,” the premier episode of the final season of Mad Men, it’s from the front. His hair is lacquered and immaculate. A cigarette smolders idly between his fingers. His shirt is blue. His tie is striped. Avert your eyes and defend against spoilers if you must, but I feel obliged to inform you that he is not wearing a jacket.

The more things change, the more one thing stays the same: Don Draper. He was fucked up and womanizing at the start, and he’s back at it again on Sunday night. While other prominent characters have been buffeted by the winds of fate — some lost jobs, others their lives, and a vast majority of them have suffered sideburns — Don remains steadfast and opaque. He looked like an astronaut in 1960, with his monochrome tailoring and his sharply cut jib. Wearing the same clothes a decade later, he looks more like an alien. Perhaps the most remarkable thing about Mad Men as it heads into the home stretch is that it took a decade that exists in the American imagination as a kind of terrifying luge and recast it as a slow, fatalistic sink. Fashion shifts, morals adapt, wives leave — but Don stays splashing around in the same lukewarm bath of bourbon and vice. Remember the season he spent attempting to swim his way to better health and sobriety? The truth is, he just got very good at treading water.

Don’t get me wrong: I’ve always admired creator Matthew Weiner’s dedication to this dispiriting personal stasis, even when it has resulted in frustrating art. Don’s paralysis is a far cry from that of Tony Soprano, his direct predecessor on Difficult Man Mountain. David Chase, Weiner’s mentor and friend, was famously cynical and bitter about the possibility of transformative change — a pre-Sopranos life spent in the trenches of network TV will do that to you. And so, from ducks to dawn, in therapy and out of it, Tony remained incapable of self-reflection or betterment. The world was out to get him, so what use were mirrors? Mad Men is different. Though it may not always appear obvious, what with Don’s infinite cycle of bingeing and purging and the way the Sterling Cooper office in Manhattan may as well be the Hotel California, the truth is that Mad Men is a show that believes deeply in the possibility of change. It’s just under no illusions about how difficult that process can be.

Consider, if you will, how last season concluded. (And, with all due respect to AMC, the episodes that aired in 2014 and those beginning Sunday truly are distinct seasons, no matter what sort of linguistic games the network had to play to avoid violating anyone’s contract.) In a delirious 24-hour period, a human being set foot on the moon, Bert Cooper died, and Roger Sterling pulled one last trick out of the bottom of a bottle: By selling the company to McCann Erickson, Roger saved Don’s job, made everyone rich, and bested Harry Hamlin’s slick Jim Cutler. Improbably, Don’s dearest wish was once again granted: a return to the comfortable status quo.

Yet the episode didn’t end with Roger’s triumphant speech on the second floor. It ended downstairs, where Don was at first dazzled and then dazed by a hallucination of Bert Cooper singing and dancing about how the best things in life are free. In that otherworldly light, Jon Hamm’s bright eyes looked glassy and hollow. Yes, Don had gotten what he wanted, but, for an alcohol-swigging alpha male in the Nixon era, this alone was hardly noteworthy. What skittered across his face in that moment was the buried realization that maybe he had once again passed up what he needed. The tricky machinations required to pull off the umpteenth office coup obscured how easy it was for him to let Megan — and, by extension, the warmth of California — slip away. The day after man escaped the bonds of gravity, Don Draper was once again trapped within his own heavy condition.

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“Severance” picks up this baton and twirls it in surprising and often elliptical ways. (Relax, Matthew Weiner and Matthew Weiner’s attorneys: I’m not going to say exactly how.) At first blush, it feels more like a reboot than a last hurrah. After a second viewing, though, a darker momentum is revealed. “Severance” is an episode built around paths not taken and heartfelt advice ignored. Beneath the office politics and ever-widening lapels is a steady drumbeat of uncomfortable truth: that the greatest impediments to personal change always come from within, not without. External forces intrude, from assassinations to love-ins and back, but no matter who we are — or, better, when we are — the trip wires stay the same: vanity, resentment, fear. To see Don and Roger boozing and catting, still up to their old tricks after eight years (in the real world; it’s been longer for them), is nostalgic, but in the painful, literal sense we learned about in Don’s most famous pitch. The noble carousel of Mad Men’s first season has become a hamster wheel. It’s the great tradition of American sitcoms to suggest that there could be nothing better than keeping the gang together, season after season, for adventure after adventure. It’s the great legacy of Mad Men to suggest that maybe this sort of comedy, in the fullness of time, begins to look more and more like tragedy.

Is this the story Matthew Weiner has been telling since the beginning? In a way, yes. The most obvious remaining question for these final seven episodes is what will become of Don. But this is no different from the big questions that blink like warning lights atop our own lives: How will we live? When will we die? Can we ever find a way to be happy on our own terms? It’s a very contemporary notion, this idea that prestige TV series all have one core story to tell. It’s the sort of framework that makes sense for expertly constructed diving bells like Breaking Bad or the new breed of limited series like True Detective and Fargo, but not something as intentionally digressive as Mad Men. TV storytelling is rarely a perfect, arcing javelin toss. It’s more like a spilled cocktail, soaking everything, in all directions all at once. I promise you that wherever we end up six weeks from now wasn’t the planned destination when we embarked. And that’s a good thing. Circumstances change often and easily, even if people don’t. As Peggy and Don both know, the last idea is often the best. When you’ve been at it long enough and the sun is almost up and the bottle is nearly empty, all that you’re left with is the truth.

If Don Draper enters these final episodes as a man out of time, his show finds itself in similar straits. In an era buzzed on resolution and binge-watching, Mad Men may be the last high-profile drama granted the freedom to drift along into a dreamy, idiosyncratic conclusion. In 2007, when the series premiered, its uncompromising focus on internal battlefields felt radical but of a piece with the sort of ambitious storytelling unspooling elsewhere on the dial. Now, with literal battlefields ascendant, it feels like a relic. The culture appears to have moved on: Mad Men hasn’t won an Emmy in years and its ratings, while never robust, have sunk. I say this not as a referendum on the show’s undimmed quality — it is unquestionably one of the best and most daring series of all time; its afterlife will outlast Sally Draper’s grandkids — but more as a reflection of the shifting sands of style and taste. Audiences today hunger for payoffs and meaning: We demand to know where Sal ended up; whom Peggy might marry; if, for God’s sake, anyone will ever actually jump out of that high midtown window. We do this even though we know that the answers would diminish the magic and contradict Mad Men’s essential worldview: that real life occurs between history’s signposts, without much rhyme and with precious little reason. That the drink, once mixed, can never be poured back into the bottle.

Despite its period setting, Mad Men has never been a particularly old-fashioned show. Yet I find myself marking its passing with an antiquated desire to see it continue indefinitely. If there is no obvious ending, why force one at all? Couldn’t it spin on for years, like a whiskey-soaked CSI? All the crime scenes would be subjective; all the evidence emotional. Can’t we linger a while longer under the harsh fluorescent lights of a fast food restaurant with our surrogate friends, our pretend family? Like Don, I refuse to think rationally here. I want it all to stay unchanged. But in a few short months, he and I are likely to be taught the same hard lesson. The calendar doesn’t wait for us to get what we need, to make better decisions or to clean up our messes. The calendar doesn’t wait at all. And, unlike that infamous carousel, it never turns back to the beginning. The last page is about to be revealed.

Filed Under: TV, Mad Men, AMC, Jon Hamm, Matthew Weiner, david chase, The Sopranos

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Andy Greenwald is a staff writer for Grantland.

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