mine: mad men

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In honor of Mad Men coming to an end, I thought I’d post these old things. These were my final project for my Entrepreneurial Illustration class at CCAD my junior year. After flip flopping a few times on my subject matter my teacher told me “Don’t fuck this up. I like this show”. Needless to say, that scared me enough to binge watch all three of the seasons on netflix and catch up.

These are two of my favorite pieces and I think they were the starting point of me attempting to specialize in portraiture. (that’s what I like to think). 

Mad Men Finale: Dissecting Don Draper’s Story

SPOILERS SPOILERS SPOILERS AHEAD! This post will contain spoilers for Mad Men up to and through the series finale. DO NOT READ IT UNLESS YOU’VE SEEN THE EPISODE.


It’s probably pretty safe to say nobody was expecting exactly what went down in Don Draper’s storyline during the Mad Men series finale on May 17th. The rest of the episode provided satisfying closure for most of the other main characters, but I’m not going to spend time there because the controversy is pretty squarely focused on Don.

First of all, let me do a quick outline of the way I see Don’s storyline up to this point. Series 1 of Mad Men introduced us to Don Draper, an ad executive at the top of his game. For a while, he held things together, but very quickly, we saw his identity begin to crumble. Even as he prospered financially, his personal world shattered in the wake of his unfaithfulness and substance abuse. The thing about Don, as Matthew Weiner showed us slowly over seven seasons, was that he was forever motivated by a search for fulfillment he could never find. 

We were shown, over and over, flashbacks of an abused, neglected, and hurt little boy who became a young man who thought his only hope of happiness was to become someone else. And yet, even as Don Draper got everything he thought he wanted, it was never enough. By season six, Don was reading Dante’s Inferno and had fallen into his own version of hell on earth. At first, he grasped at his failed identity, but once it had been pulverized, like Humpty Dumpty, it was never the same.

The story of the final season, particularly its second half, has been the story of Don shedding the last vestiges of an identity he’d come to know would never give him the fulfillment he’d always craved. He shed his suit, his possessions, his dignity, and finally even his transportation.

One of the most poignant images of the next to last episode was Don watching a young, good-looking, would-be conman drive away in his car. As with so much of Matthew Weiner’s writing, this was obviously symbolic. It’s Don Draper watching the youngest version of his fake self leave his life forever. This left us in an interesting position going into the finale, an almost wide-open place without much to go on, just a smiling man without an identity sitting on a bench.

The finale itself, where Don is concerned, was a poem—about identity, self-worth, and what it means to really be human. At first, jarringly, it seemed like not a lot had changed. Don was still bedding women, being pleasant to people, and overdoing it with alcohol. I spent several minutes wondering what in the world this could mean, given the character development we’d seen previously.

Enter Stephanie. The one thing I accurately predicted about the finale is that there would be a callback to Anna Draper’s niece, and there was. Don went to her house, obviously hoping to find the same kind of unconditional love her aunt had provided—the one thing that had actually afforded him a measure of personal healing in the past. Instead, he found another damaged person in need of help.

The only thing Stephanie did was to drag him along to a spiritual retreat. Here’s where things got so symbolic that the meaning was shouting louder than the words. Like Dickensian ghosts, the retreat attendees, through different sessions, reflected back to Don his own view of himself. In one exercise, as other attendees revealed their opinions of one another nonverbally, other pairings hugged and touched gently. In contrast, the elderly woman opposite Don pushed him, angrily and forcefully. In another difficult session, Stephanie revealed her feelings of the world judging her and then told Don that the worst part was knowing that the judgments were right.

The meanings here were clear: The old woman’s animosity was Don’s own self-hatred, and the feeling of being justifiably judged by the world is exactly how he went through life. The symbolism got even thicker as Don found out he couldn’t leave the retreat. He was stuck there, just as he felt stuck in himself. He revealed as much in an emotional phone call to Peggy that made me wonder for a split second if he was going to end his life. The meaning of this call was significant to Don because his last external hope, the woman who once bailed him out of jail and had saved him professionally more than once, failed. Peggy tried to be encouraging, but she couldn’t save him.

Obviously feeling hopeless, Don followed a retreat leader into a group session. The first story shared was a mundane one about a man’s failed marriage. And then an average-looking man sat down in the hotseat. This man was, obviously, the anti-Don. He wasn’t handsome, he didn’t seem particularly clever, and he was clearly not all that successful.

Beginning to speak, he wove a tale of working in an office, of feeling insignificant, of always thinking no one cared about the real him. The crux of his story was the revelation that he didn’t even really understand what he was desperate for, so he was unable to receive the love others tried to give him. As he listened, Don’s face changed, and when the man finished, in tears, Don went over to him and embraced him, and they wept together.

What is happening when we reach this point? For the first time in Mad Men, we are seeing Don Draper as he sees himself. Throughout seven seasons, we have seen people fawn over Don for his looks, his money, his talent. In every way, he’s come across as extraordinary. But when Don Draper looks in the mirror, that’s not what he sees. He sees someone as average and miserable as the man in front of him, devoid of the fulfillment he so desperately craves.

The mystery is solved; we as a viewing audience now know who Don Draper sees when he looks inside. But this revelation is for us; what’s happening to him? Don spent most of Mad Men literally and metaphorically running away from Dick Whitman, a life he hated, but ultimately coming to hate Don Draper just as much. He forever loathed himself for still longing and needing and being broken.

His embrace of the other man is, finally, an embrace of himself. His epiphany comes when he finally sees himself reflected in someone else and realizes that he finds that person worth loving. He doesn’t have to have Anna Draper’s unconditional love any more. He can live without Peggy’s validation. He can even be a real father to his children.

Why? Because his journey hasn’t ended; it’s begun.

Don Draper has finally realized something we all have to confront—that to even start walking the path toward true fulfillment, you have to look yourself squarely in the eye with a full understanding of your imperfections and gaping holes and instead of trying to cover up or smother that needy, unbeautiful self to death out of shame and hatred, hold it close with merciful love. This is how each one of us becomes an authentic self, and it’s how we begin to find a way to truly connect with and love others. 

Much debate is already raging about the very end of the episode, the Coke ad. Some think Don created it. Others think Peggy did. Still others (me included) think it’s symbolic, rather than a literal event in the narrative. Ultimately, it doesn’t matter. Don Draper’s story, at its heart, was never about making ads. In Mad Men, advertising was always about the ways we represent ourselves and our lives to the world and how we use our ideas of people and products to unsuccessfully fill the longings inside of us.  It was always a huge amount bigger than a jingle on TV or a picture in a magazine.

In the end, Don had his epiphany in a retreat session thousands of miles from his Manhattan office building. If that epiphany led to the Coke ad, great. If not, who cares? For Matthew Weiner, advertising was always a metaphor for living. In the Mad Men finale, the ultimate ad man finally learned to live an authentic life. What better way to accentuate that moment than by ending with one of history’s most important ads?