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How season six of Mad Men blew up the show and set the stage for its end

Zack Handlen: Don Draper doesn’t exist. In Mad Men’s later seasons, it seemed that Matthew Weiner and company should have left the Dick Whitman/Don Draper conceit behind. It made for a great story hook at the beginning, something to hang all the period nostalgia and corrupted elegance on, but as time went on, the hook threatened to become a gimmick. It’s a little like Tony Soprano going to see a psychiatrist; brilliant at the start, but less revelatory as the world those sessions were designed to illuminate comes into its own. Don having a secret past, Don flashing back to his miserable childhood, Don being the definition of a self-made man—it was all very symbolic and what not, but, you know, we got it. As season six kept piling on trips to the old-timey whorehouse, the dualistic identity looked more and more like an indulgence Weiner was unwilling (or unable) to let go.

But as the season finale reminds us, the most important truth within all this convolution remains relevant: Don Draper doesn’t exist. He’s a figment, an ideal, a concoction built by a fundamentally passive coward in response to his own desperate need to put the past behind him. The life Dick Whitman built for himself was built on a factual and psychological lie, a surface illusion that relied on forward momentum to sustain itself. There’s a bit back in season one that always stuck with me: not the carousel speech, as heartrending as that is (that’s a great piece of writing because it makes us want to believe in the con—we’ve been enjoying Don’s sexy exploits, and now, all of a sudden, he’s given himself a soul), but his sudden, impulsive desire to run away. Pete Campbell has found out his secret, and Don’s first reaction is to bolt. But he can’t do it alone, because Don Draper can’t exist alone. He needs someone else to believe in him, someone else to sustain the myth. So he runs to Rachel, and Rachel, maybe the first out of anyone, sees him for what he is: a ghost. A nothing. The mystique, the bluster, the relentless need for control, is just a shell game to hide the brokenness at the man’s core.


In a way, the past five seasons have been about sustaining that shell game for as long as possible. Creating new companies, new relationships, new successes—just to keep the image afloat. Back in season four, Don flirted with revelation (literally) in the form of Dr. Faye Miller, but their relationship was an impossibility. I was disappointed when Don chose Megan over Faye, because to me it indicated dramatic stagnation, and in a way, season five reflected that stagnation, its bold stylistic innovations working to distract from the fact that these were short stories all building to a familiar end. Don Draper has to keep moving, because if he doesn’t keep moving, he dies, and that leads to the affairs, the rapacious appetite, the refusal to accept good enough. In retrospect, it’s doubtful marrying Faye (if that was even on the table) would’ve helped. A romantic partner doesn’t help you solve your own problems. At best, you choose someone who reflects the part of yourself you most want to hold onto. Megan was youth, optimism, the modern life. Marrying her was Don trying to recapture his gift for reinvention, trying to be honest without accepting the past that honesty would demand from him. It failed because Dick Whitman and Megan Draper have nothing to talk about.

So that brings us to season six. Todd, you’ve talked about how Mad Men is more of an anthology than its serialized nature would suggest, and I thought that was especially true of season five; to me, though, season six was as close to a novel as the show’s gotten, which may explain why it was so frustrating to watch. The first episode sets up the arc: images of death, of collapse, prevail. There’s a lot going on in these 13 episodes, and I don’t want to suggest that Don’s the only part worth talking about (Peggy and Pete went through a lot, and who can forget the magic of Bob Benson?), but his behavior in the finale really brought home what, to me, is the central storyline of the season: the death of Don Draper. I don’t mean the name is gone for good, or even the persona, and we won’t know until next year just how deep the changes go, but surely something is different. That Hershey pitch was remarkable, and so fundamentally un-Draper-like. He opens with the usual bullshit about the past, creating an image of the boyhood he wanted so badly. It goes over well enough, but it’s crap, and you can see on his face that he knows it’s crap. (Hamm’s performance here is just fantastic.) So then he decides to actually be Dick Whitman, in public, in front of everybody. Same Draper confidence, same Draper eloquence, but this time, with the absolute, scarifying truth. It’s a powerful speech, and much of its power comes from the way it’s completely at odds with what the people in the room expect and need from him. This is the antithesis of the Draper pitch. This is the carousel speech that has photos stuck in the slides of child abuse and of whores fucking. All season, Don’s been pitching absences, emptiness, holes in the center of the world, and finally, he decides to fill the space. The result is the loss of his job, which might be the best thing to happen to him in years.

But who knows; maybe this is just one more last-ditch stall. Do you think I’m being overly optimistic, Todd? And what were some of your favorite character moments from this year? (I would watch a show that was just Christina Hendricks doing her old Jewish lady voice for an hour every week.)

Todd VanDerWerff: As I said in my review of the finale, I really do feel like this is the show setting itself up for its end game in an exciting way where nothing can ever be quite the same. I’ve read all of the interviews Matt Weiner did with other publications (ahem), and in all of them, he says he doesn’t know where this is all going to end, but I’d bet he knows he’s given himself a lot of room to play with as season seven begins, and that’s often when he does his best work. Unlike you, I thought season five was one of Mad Men’s finest seasons, because the relative stability of the show’s format meant that Weiner and company could just experiment with whatever they wanted. The lack of structure—outside of a general sense that the show was about advertising in the ’60s—was what gave it the freedom to be so daring and unconventional.


Which is why I sort of pushed back against season six at its start. It was obvious from the first that Weiner was taking this story somewhere, and I don’t know that novelistic construction is Mad Men’s strongest suit. Breaking Bad works best in that mode because the whole story is this complicated, driving notion of what’s going to happen next, and that’s what gives the show its freedom. Mad Men is about the fillips around the edges of life, and any time it starts to get too rigorous, the air gets let out of everything just a little bit. Yet damned if the season didn’t have its hooks in me by the end, if the whole thing didn’t add up to something greater than the sum of its parts, where season five ended with a finale that made me think maybe the whole season had just been a series of experiments to see what would and wouldn’t work. Season six felt purposefully constructed in a way no other season of Mad Men has, with every single strand leading to that moment when Don looks at his daughter, hoping that she will understand even a small piece of who he actually is. Along the way, we got doubles and deception and the truth being revealed. We also got a nation in chaos and an office that reflected that, as well as everyone coping with having to grow up into the next version of themselves.

And we got Don as a raging asshole, an arrogant prick who spent most of the season belittling people and forcing Peggy into worse and worse positions. (And then, of course, how does her arc end? With her turning from the camera and reflecting the pose from the end of Mad Men’s opening credits. She is becoming him, like it or not, as we so often become our parents, even our metaphorical ones.) You asked me for my favorite character moments, and I could talk about Peggy stabbing Abe or adopting a cat, or I could talk about any number of amazing Vincent Kartheiser line readings (the finale’s “NOT GREAT, BOB!” chief among them), but every time I think about this season, I’m going to come back to Don Draper. The season really reoriented the show as being one about him, in a way that seasons four and five kind of drifted from. I think you’re right that the series was playing out a string it might not have even realized it was until the gut punch of “In Care Of” offered up all sorts of emotional catharsis. You ask for a character moment? All I can think of is Don walking away from the camera at several points this season, receding from people, first as a cocky asshole but then getting eroded down into something more pathetic and small but also something more human.


To be honest, that was the thing so many of us—myself included—pushed back against. So Don hadn’t learned his lessons? So what? We had to watch him be a dick over and over again, to everybody in his life? As it turned out, yes, we did, because we needed to see how he could be brought so low—and I love the series’ confidence that we will intuitively understand this without it having to point very much out at all, like the increasing insert shots we got throughout the season of Don adding alcohol to his routine, culminating in that early finale shot of him adding it to his morning coffee. Novelistic construction still isn’t Mad Men’s best side—there are plot moments throughout the season that strain credulity, and one can occasionally feel the writers forcing the characters into particular positions just to make sure everything happens exactly as it should—but it also brought the series to what might be its strongest season finale (give or take a “Shut The Door. Have A Seat” or a “The Wheel”).

What’s more, by putting this particular story at this particular juncture, Mad Men has opened itself up so much that the final season can be about literally anything. I’m guessing advertising and the ’60s will be involved somehow, but beyond that, the sky’s the limit—appropriate for a story that could very well take place around the time of the moon landing.


But I write about this show every week, Zack. I want to know when you started to sense all of the pieces of this story coming together in a satisfying way. I’m ashamed to say I didn’t really feel it until the penultimate episode, and now that I know what was happening, I’m feeling pretty dumb about missing some of the coalescing, having thought I knew how this show told stories (obviously, I didn’t). And while we’re at it, what do you make of “The Crash,” one of my favorite episodes of the season and one I increasingly see as a Rosetta stone to understand the whole damn series?

ZH: One of the luxuries of not writing about this show week to week is that I get more time for my opinion about individual episodes to coalesce. This year, I found myself falling back into a habit I’ve had with Mad Men ever since the second season, missing episodes and then having to catch up with everything on my DVR before diving into the reviews to try and piece together what I’d seen. Week-to-week makes it easier to miss the forest for the trees, so when I say I thought this season’s Asshole Don arc was building toward something fairly early on, that’s more the function of insightful writers like you and half a dozen other TV critics than it is some sort of cleverness on my part. Around “For Immediate Release,” when Don goes full Draper, booting Jaguar to the curb and merging ad companies, it started to look like all this misery was part of a design bigger than the immediate moment. After all, he was just doing what he’d always done, but the results were, while thrilling, less than triumphant. Don’s mojo has been draining away for a while now, but to see him back on his game and have so many people bitter about it was telling.


That said, I had no freaking idea it was all building toward what we got in the finale; from what I can tell, few people did, which may be what impresses me most about the season, at least on a structural level. So much of the talk this year has been about Don’s loathsomeness, about the misery the show seems to be piling on its characters; it was the kind of slow burn that takes an audience’s investment and seems to punish them for caring. All the usual sources of entertainment, the melodramatic romances, the corporate intrigue, the crazy drug trips, felt drab, small-minded, petty. There were still thrills, but they kept getting dragged down by a sour taste that wouldn’t go away. Something was rotten, and no amount of maneuvering, backbiting, and fucking around was going to take that away. And while that ultimately paid off, Weiner and his writing staff showed a lot of faith in their audience’s willingness to stick around. If Don’s bottoming out in the last two episodes (prompted, I think, by Sally’s discovery of his affair) hadn’t delivered two of the best scenes of the season—the Hershey pitch and “This is where I grew up”—this could’ve been a disaster. 


It wasn’t, though, partly because of the strengths of that finale, which snapped everything into focus the way Mad Men finales so often do, and partly because of signposts strewn along the way that hinted at what was to come. And of those signposts, I’m with you: “The Crash” was the key. The episode’s apparently loopy, “throw it at the wall and see what sticks” approach pulls itself together beautifully when viewed in hindsight, going a long way toward justifying both the season’s copious Dick Whitman flashbacks and Don’s disintegration. In the present, a drug-fueled Don is pawing through old copy, searching desperately for the key that will explain everything that’s gone wrong in his life, while at home, Sally is dealing with an intruder who drives home for her how little she knows about her father; in the past, a young Dick gets one of his few exposures to maternal love from a prostitute who nurses him back to health, only to have that prostitute force herself on him as soon as his fever ebbs. It’s a toxic Freudian stew that transforms six seasons’ worth of fragmentary, occasionally pathetic love affairs into a kind of reflex action. Sex is the only love Don understands, and he despises himself for reaching for it. The deeper he buries his childhood, and the more he tries to re-create himself as the man he thinks he needs to be, the worse it gets, because the foundation is fundamentally flawed, a dream created by a lonely boy. His illusion, built on an intoxicating cocktail of commerce and fuckery, is a fast car with no headlights, and sooner or later, there’s gonna be a brick wall.


So, yeah, I keep coming back to Don, too. But there were other high points: While dragging Peggy back into the Sterling Cooper Draper Pryce orbit looked like an odd choice, putting her in Don’s office at the end was one of those reversals that didn’t lose any of its power through its inevitability. Her team-up with Joan, while brief, was one of the season’s most cheer-worthy moments, demonstrating how even as some fortunes collapsed, others were rising. Even small moments like her semi-drunk conversation with Pete Campbell reminded us of the depth of the show’s history, and the way the writers have of finding warmth in the unlikeliest of places. As for Pete, he had an arc that in some respects mirrored Don’s own, a disastrous affair with an unstable young woman leading to the apparent end of his marriage, combined with the constant pressure to perform at a job where no one really respects his efforts. That’s always been Pete’s story: so much of Don’s angst, so little of his allure. But as odd as the death of Pete’s mom was (Matthew Weiner all but confirmed that Manuelo murdered her, which, what?), and as embarrassing as it was to see him lose once again to a handsome climber, he is, as Trudy tells him, free. Pete and Don, office pariahs, broken homes, but maybe in a place that will let them find some peace. Meanwhile Peggy has the career she dreamed of, no love in her life, and a cat.

But Don, man… I can see how Don’s confession to the Hershey’s people could appear contrived, but to me, it fit perfectly into the way he’s always gone, operating more on impulse and intuition than calculation. He’s still selfish, he’s still short-sighted, and he still expects to get what he wants. (I love how Hamm plays that final confrontation with the partners; there’s some bluster, but it’s almost like he’s objecting on reflex. He knows they have him cold.) But now there’s some glimmer of hope that maybe all this destruction might let him find his soul.


Before we get into looking forward to the final season, though, is there anything you think works better looking back now than you did when you first saw it? Anything that doesn’t? (Seriously, Pete’s mom got thrown off a boat?) And what did you think of the rise of Betty Francis? 

TV: I appreciate that Matthew Weiner thinks I should have grasped intuitively that Joan succeeded with the Avon account, but I really would have loved even a line of dialogue clearing that all up. And I’m incredibly fascinated by the seemingly aborted arc of Ginsberg losing it. He’s deeply affected by the assassination of Martin Luther King Jr., and then he seems like he’s completely falling apart as the rest of the season goes on. But the show mostly just loses track of him after that surprisingly touching scene where Bob tried to talk some sense into him. What happens next? Who knows?


Now, granted, I didn’t need to see where Ginsberg gets to after that moment. Now that I’ve seen the whole season, I realize that he wasn’t building to anything in particular and was, instead, just there to offer us a taste of the swirling chaos that was devouring everyone in Don’s life. But the swirling chaos worked better with some characters—Peggy—than it did with others—Megan. In fact, I’d say that looking back on the season as a whole, Megan comes off as the character who benefits the least from examining the epic sweep of the storytelling. I was a staunch Megan defender in season five, and I like Jessica Paré’s performance. But I can’t say that Megan was truly important to the story of the season, and the story the show tried to give her about her soap-opera career was fine but also felt like it had very little to do with anything.

Compare that to Betty, who has even less story-based reason to still be a part of the show but felt more integral here than she has in any season since season two. (Yes, she was still married to Don in season three, but that season felt like such a repeat of her arc in season two that I began my general Betty frustration earlier than most.) Betty’s arc this season is of a woman who’s regained the power she felt at her most attractive and of a woman who’s been through enough now to know what she wants and how to get it. That scene where she talked with Don in bed after they’d hooked up was one of the best of the season, and she gets to seem wiser than Betty ever has before. We see Betty so often through the eyes of Don and Sally that it sort of makes sense that she would inspire such consternation from fans, but I liked the little glimpses we got of an increasingly confident, increasingly on-the-rise Betty, who’s found a measure of happiness and clung to it as much as she can.


I also can’t talk about the season as a whole without talking about Ted Chaough. I was genuinely surprised by how much the show got me to buy into the attraction between him and Peggy, particularly in the last couple of episodes, when I had more or less found it to be an unnecessary romantic complication earlier. But Ted and Bob both represent spins on a more modern kind of man, the sorts of guys who are more in touch with their feelings or more eager to please and, thus, will rise in a more emotional ’70s and ’80s, when the political reforms of ’60s left-wing movements will mostly have crumbled to ash but the general vibe and good feelings will have seeped just enough into the mainstream to make everybody want to feel good about themselves. Don talks about Ted as if he’s some sort of Draper aping grotesque who doesn’t yet understand that he’s just the same as the other creative director, but it seems clear to me that Don doesn’t quite possess what it would take to even understand Ted. This is perhaps wishful thinking, but I like to think that being around someone so open and earnest as Ted has somehow made Don more capable of making that revelation about his childhood in the Hershey meeting—and he does so only after first looking at Ted. Something about Ted brings out the vulnerable in Don, and that makes him all the more self-destructive, resulting in the long string of events that lead to both his downfall and his potential for redemption. If I’m rewatching this season (and I hope to), I’m keeping a close eye on the interactions between these two.

But I’m also keeping a close eye on what Weiner and company seem to be building for the road ahead. Weiner claims he has no idea what season seven looks like (outside of a vague idea for a final image), but I’m willing to bet that he already has a few small ranges of possibilities to indulge in. What I’ll ask, then, isn’t about story but about theme and character and mood: What do you want from the final season of Mad Men? Not in plot specifics but in the idea of what vibe you might like to get from the show as it closes out its run? And which of the show’s many different selves do you hope it most engages with in its final stretch?


ZH: It’s always difficult to try and parse out what I want from a show, because I’m almost always of two minds on the subject: The fan in me wants a happy ending with everybody hugging and maybe there’s some ice cream, while the, I don’t know—critic? Guy who loves stories?—wants something more complex. With Mad Men, it’s hard to imagine a final season that isn’t at least a little bittersweet. Weiner and his staff have always done a great job at closing out each year with a kind of definitive stamp or image that reshapes how we think of everything that came before it. Last year, it was “Are you alone?” This year, it’s “This is where I grew up.” Out of any great show on the air right now, I have the most faith in this one getting it right. There’s no significant plot to wrap up, no hanging questions of mythology to resolve. That freedom carries with it a certain amount of responsibility, but at the same time, it means people aren’t going to get pissed off by some random hour about Don and a mystical wellspring of all life in the universe. (Though that would be amazing. Maybe we’ll see an episode about Don and The Whore traveling the countryside, solving mysteries!)

What “getting it right” means to me, though, is hard to pin down. What I value most about this show are its moments of incredibly hard-earned connection. “The Suitcase” comes to mind, as it so often does when talking about Mad Men at its best; it’s something that seems so simple and straightforward, but is incredibly difficult to pull off effectively, because there needs to be a constant understanding of the difficulty and cost of those open moments. There were a few this season, between Peggy and Joan, and Peggy and Pete, arguably Ted and Don (though those tended to be one-sided), and of course the ending. The clarity of these exchanges, the impression that we’re getting glimpses of a person’s true self, striving to be seen, is deeply moving, especially in the context of all the white noise that surrounds them. So I want more of that, really. I want to get a piece of all the show’s various selves—the intrigue, the sudden weird twists, the romance, the symbolism—but what I want most is two people in a room, talking, with a little hope that whatever happens next might not be so terrible.


How about you, Todd? And what drug do you think Don will get injected in his ass next year?

TV: Well, clearly, it’s time for Don to embrace the cleansing powers of the blue crystal meth, because this show and Breaking Bad are going to merge into one show and run forever and ever and ever! (Not that we would want them to, of course.)


I tend to agree with you on those moments of connection. They’re the things that drive this show, and there’s good reason that I’ve always wanted the ultimate resolution of the Don and Peggy relationship to be a firm, mutually respectful handshake between the two of them. (What? I can have dreams, too!) I guess if I had a fear about the final season, it would be that these moments would arrive with too great of frequency. The show has always been so expert at spacing these moments out, so that they arrive irregularly enough to make them seem transformative when they do but just regularly enough to keep us watching, hoping for the next fix of real, raw connection.

Beyond that, I don’t know. I love final seasons of long-running TV shows, and I love the way that they wrap up stories we didn’t even expect to turn into stories. I’d love for Betty to get even more to do. I can’t wait to see how Sally winds up. I’m hopeful that Megan returns, even if plenty of fans seem to wish she wouldn’t, and I would love to hear from some of the characters who have disappeared along the way, like Paul Kinsey and, yes, Sal. Most of all, I just want to see where this series leaves Don. The prediction all along has always been that he will leave the series as he “entered” it, by plunging from the top of a building, losing his life while surrounded by the symbols of the fake lives he constructed for others to luxuriate in. But that would be too easy an ending and, weirdly, too safe of one. Don Draper has finally begun to know himself; in season seven, I hope that process leads him to moments of insight and maybe even growth. Death haunts this show, but it isn’t the point of it. The point, ultimately, is all about life, and that’s where I want these people to be when it ends: alive and uncertain, the future a thing that we know but they can only guess at.


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