“Utopia – The Place That Cannot Be”: How Mad Men Incorporates the Divine Comedy Into the American Dream

“They taught us at Barnard about that word, ‘utopia,’” says Rachel Menken (Maggie Siff) in “Babylon,” the sixth episode of Mad Men’s first season. “The Greeks had two meanings for it: ‘eu-topos,’ meaning ‘the good place,’ and ‘u-topos,’ meaning ‘the place that cannot be.’”

Mad Men has spent much of its runtime preoccupied with this idea of the unattainable utopia, with Don Draper (Jon Hamm), Pete Campbell (Vincent Kartheiser), Peggy Olson (Elisabeth Moss), and the rest chasing after that most fleeting and elusive of commodities: happiness. It’s no accident that a series set in the advertising industry finds its characters unable to grasp genuine happiness. After all, the idea of advertising is antithetical to lasting happiness. It’s a career dedicated to selling facsimiles of happiness. As Don says in the series’ pilot:

“Advertising is based on one thing: happiness. And you know what happiness is? Happiness is the smell of a new car. It’s freedom from fear. It’s a billboard on the side of the road that screams reassurance that whatever you’re doing is OK. You are OK.”

Mad Men is indeed based on happiness, yet contrary to Don’s thesis, happiness is not a product that can be bought. In fact, as the series approaches its conclusion, the ability of Don or anyone else to find lasting happiness is very much in doubt.

“I keep going to a lot of places and ending up somewhere I’ve already been,” Don says in the opening episode of season three. Indeed, throughout the first five seasons of the show, Don’s inability to find contentment consistently returns him to the unfulfilling comforts of hedonism.

Yet this hedonism, and its accompanying lack of attachment, prove entirely insufficient to ward off Don’s unhappiness. “This never happened,” he tells Peggy after she gives birth to a baby, urging her to move on with her life. “It will shock you how much this never happened.” Yet Don’s quintessentially American philosophy of relentless forward motion proves unsatisfying to him. “We’re flawed,” Don muses in season four, “Because we want so much more. We’re ruined because we get those things and wish for what we had.” The specter of nostalgia looms over the world of Mad Men, as characters inexorably marching into the future are consumed with longing for the past.

Perhaps the most radical example of change occurs in the season three finale, in which Don divorces his wife and abandons the agency where he works in order to start his own. Over the closing credits, Roy Orbison sings, “The future is much better than the past.” Yet for all his reinvention, Don’s future looks much the same as his past. He may have changed his life, but he has failed to change his self, and so, two seasons later, the end of season five finds Don returning to his old ways as his second marriage begins to fail. As Nancy Sinatra sings, “You Only Live Twice,” Don sits at a bar. A beautiful woman asks, “Are you alone?” Don only smiles. Weiner cuts away – we know the answer already.

“Midway Upon Our Life’s Journey…” : Don’s Inferno

Thus, season six opens with Don having achieved everything he ostensibly wanted, living in a vision of hedonistic paradise – lying on a sun-drenched beach in Hawaii, successful in his professional life and with a beautiful young wife on his arm. And yet here we find Don reading the opening lines from Dante’s Inferno: “Midway in our life’s journey, I went astray from the straight path and woke to find myself in a dark wood.”

Here, surrounded by the success of the American Dream, Don has worked and fought to attain complete hedonistic bliss – and here, having come full circle (a fact hammered home by the sixth season’s repeated callbacks to season one), Don finds himself gripped more tightly than ever by existential dread and ennui. In fact, within the very first episode, Don touches base in each of hell’s nine circles – starting on the beach, in Limbo, and culminating in Treachery, as he has an affair with his neighbor’s wife, Sylvia (Linda Cardellini) – whose name, “forest,” literally recalls the “dark wood” from Dante’s opening line. From here, Mad Men follows the arc of the Inferno: Don descends deeper and deeper into sin and self-loathing as he comes to more and more thorough self-knowledge – and only once he hits bottom can he begin to move up.

The season six opener, “The Doorway,” is shot through with a tangible sense of malaise, brought on by the overhanging reality of death. The episode opens with a brief, jarring POV shot of a resuscitation, performed by someone we later discover is Sylvia’s cuckolded husband, Arnold Rosen, a heart surgeon.

This vignette sets the stage for an episode full of characters who are finding themselves lurching ever closer to mortality. Roger Sterling (John Slattery), the agency’s most incorrigible hedonist, finds himself confronted by the death of his mother. At the wake, a drunken Don, barely able to stand upright, vomits into a wastebasket. Roger, finding control of the proceedings wrenched away from him, yells, “This is my funeral!”

After returning from Hawaii, Don finds himself changed by the experience, preoccupied with an ineffable reality which, uncharacteristically, he finds himself unable to express. He pitches an opaque, evocative ad to Sheraton, describing Hawaii as “the jumping off point,” but the executives find the ad morbid. It reminds them of suicide.

“The Doorway” concludes, fittingly, on New Year’s Eve, 1968 – a turbulent year in American history, brimming with the threat of violence and death. Over the next year, Don continues to descend deeper and deeper into vice, even as the reality of death hangs overhead, bringing with it reminders of lives not lived.

One way season six makes the presence of death known is through doppelgängers – doubles, traditionally associated with death. Jim Cutler (Harry Hamlin) is a mirror of Roger, and Megan (Jessica Paré) plays twin characters on her soap opera. Duck Phillips (Mark Moses) is a mirror of Pete, the sad, pathetic loser he could grow to become. Yet everything centers on Don, who finds himself with not one but three doubles.

The most enigmatic double, and the first Don meets, is PFC Dinkins, a soldier in the Vietnam War, on leave in Hawaii. The two run into each other in a bar, where Dinkins notes, “They offer you R&R in Honolulu and you think, ‘Did anybody notice it’s the same place?’” Hawaii, a secular paradise if there ever was one, is comparable to the hellish nightmare of Vietnam. Of course, Don was a soldier once, too – in the same branch as Dinkins, the army. Over the course of their conversation, Dinkins frequently compares himself to Don: “One day I’m gonna be a veteran in paradise. One day I’ll be the man who can’t sleep and talks to strangers.” The next morning, Don gives away the bride at Dinkins’ wedding in lieu of her father – pondering, perhaps, how little he’s really changed over the years. Later in the episode, Don is the subject of a photo-shoot in his office when he finds that he accidentally switched his lighter with Dinkins, symbolically linking the two characters. Don is puzzled by the appearance of Dinkins’ lighter, and looks blankly at the photographer, who insists, “I just want you to be yourself.”

And yet, Dinkins never lives to become like Don. In “A Tale of Two Cities,” Don, on a drug trip in California (a symbol, in the show, of Don’s perpetual escape route), converses with a hallucination of Dinkins, who is now missing an arm. “My wife thinks I’m MIA,” Dinkins confides, “But I’m actually dead.” “How come you didn’t get your arm back?” Don asks. “Dying doesn’t make you whole,” Dinkins replies. “You should see what you look like.” Don then sees himself floating facedown in the pool, and wakes up to find Roger standing over him, having resuscitated him in a mirror of the season’s opening image.

Secondly, there’s Bob Benson (James Wolk), a young up-and-comer in the agency who, like Don, is living under an assumed identity. Bob resembles Don from his early days in advertising – chipper and easy to please. His relationship with Pete Campbell sets up a mirror, in the season’s penultimate episode, to the penultimate episode of the first season. In the first season, Pete discovered Don’s secret and, after unsuccessfully attempting to blackmail him, brought the facts to Bert Cooper (Robert Morse). When confronted with Bob’s secret, Pete faces the same dilemma, but chooses to spare Bob – a sign of personal growth and maturity on his part. Bob, like Dinkins, is a reminder of where Don has come from – and how little he’s changed in substantial ways.

Don’s two most important relationships are with Sally (Kiernan Shipka), his daughter, and Peggy, his protégé and, in many ways, surrogate daughter. For all of Don’s striving towards the future, Sally is a part of his past that he cannot escape, and in season six, acts as one of the few positive relationships in Don’s life. Late in the season, though, Don’s relationship with Sally is severed when she inadvertently catches him in adultery with Sylvia. This discovery shatters Sally’s perception of her father and shakes Don to his core, erecting an impassable barrier between the two. Director Jennifer Getzinger shoots their final conversation in the episode so that they are separated by a literal closed door, not even within the same shot. “Sally,” Don asks, wrenchingly, “can you hear me?” He then walks away and closes the door behind him – another boundary to authentic connection.

The next episode opens with Don, still reeling from the discovery of his sin, curled up in the fetal position on Sally’s bed. This brings us to Don’s third and most important double, Ted Chaough (Kevin Rahm), who, for the past few seasons, has been set up as the anti-Don: Don’s less charismatic competitor, the Bill Gates to his Steve Jobs. At the end of season five, Peggy leaves Don’s employ to go work for Ted – and through their relationship, Ted gains another link to Don, as an employer/mentee of Peggy. Yet this relationship also serves to further establish the two as counterpoints: where Don frequently takes Peggy for granted and even resents her, Ted is uniformly encouraging and appreciative. Early in season six, Don and Ted impulsively merge their two companies (in a conversation at a bar, mirroring that between Don and PFC Dinkins), resulting in a fierce battle of wills as Don attempts to assert dominance over the meeker Ted. Through this dynamic, Mad Men dramatizes the struggle between Don’s dark side and his light side – a struggle that Peggy points out to Don, saying, “I hoped he would rub off on you, not the other way around.”

Yet for the rest of the season, Don continues to antagonize Ted – an antagonism which only grows as Ted becomes more attracted to Peggy. Don’s jealousy for his former protégé leads him, in the season’s penultimate episode, to humiliate Ted in front of clients by making oblique references to their budding romance. Afterwards, Peggy storms into Don’s office to confront him – “You hate that he is a good man.” “He’s not that virtuous,” Don replies, cynically. “He’s just in love with you.” “Well, you killed him,” Peggy replies. “You killed the ad. You killed everything. You can stop now… You’re a monster.” His rejection by Peggy dovetails with his rejection by Sally, and Don curls up into the fetal position, having finally reached his lowest point – and it is only once he reaches his lowest point that he begins to ascend. After punching a minister, Don recalls a preacher’s words from his childhood – “The only unpardonable sin is to believe that God cannot forgive you.”

In the finale of the sixth season, “In Care Of,” Don contemplates escape again, telling Megan that he wants to move to California. Yet we know that Don can never truly escape himself that way – throughout the series, California has only been a place where Don indulged in his worst instincts. Meanwhile, Ted succumbs to temptation and promises Peggy he’ll leave his wife. Coming to Don, Ted begs to take his place in order to save his family. “I have to hold onto them,” he tells Don, “Or I’ll get lost in the chaos.” And Don finally breaks.

In a meeting with Hershey’s Chocolate, Don pitches the executives an idealized version of his childhood, telling a story of how his father rewarded him with a Hershey bar for mowing the lawn. Then he looks at Ted and decides to tell the truth:

“I was an orphan. I grew up in Pennsylvania, in a whorehouse. I read about Milton Hershey and his school in Torn Up Magazine, or some other crap the girls left by the toilet, and I read that some orphans had a different life there. I could picture it. I dreamed of it – being wanted. Because the woman who was forced to raise me would look at me every day like she wished I would disappear. The closest I got to being wanted was with a girl who made me go through her john’s pockets while they screwed. If I collected more than a dollar, she’d buy me a Hershey bar. And I would eat it alone… in my room… with great ceremony. Feeling like a normal kid. It said ‘sweet’ on the package. It was the only sweet thing in my life.”

Don immediately faces professional backlash, as he is put on leave by the other partners. Yet this bracing, cathartic honesty also opens the door to authentic connection, understanding, and reconciliation. Every season prior to the sixth ends with an image commenting on Don’s loneliness, culminating in season five’s “Are you alone?” The sixth season finally breaks the pattern, freeing Don from his cycle of lies and loneliness. On Thanksgiving, he takes his children to the brothel in which he was raised. “This is where I grew up,” he tells them.

Do You Have Time To Improve Your Life? : Don’s Purgatory

“Do you have time to improve your life?” asks Freddy Rumsen (Joel Murray) in the opening scene of season seven. It’s a thesis for the season, which follows Don through the arc of Dante’s Purgatory. He spends much of his time in season seven attempting to “fix things” with the agency in New York, while Megan, having moved to California, tries to drag him back into the hedonism symbolized by that state. The connection to Purgatory is slyly indicated in promotional teasers for the season, in which the terraces of the Chrysler Building recall Dante’s vision of purgatory as a terraced mountain.

In keeping with this theme, Freddy, a former alcoholic and now pariah of the advertising world, serves as Don’s Virgil, his guide on the path to improvement. In “The Monolith,” season seven’s fourth episode, Don has returned to work at Sterling Cooper & Partners, but balks at being subordinate to Peggy and, after antagonizing her, breaks the stipulations of his contract by getting drunk in the office. Freddy comes to bail Don out, and, in his home the next morning, fixes him a cup of coffee before giving him a bit of simple advice: “Do the work, Don.” Don takes this to heart and returns to his personal purgatory for a healthy slice of humble pie.

If Freddy is Virgil, Peggy and Sally serve as Beatrice figures – Don’s two most important relationships, and the ones that were put to the greatest test in season six. In “A Day’s Work,” Don once again opens up to Sally in a heart-to-heart conversation at a diner, confessing to her that he lost his job. When he drops her off at school at the episode’s conclusion, she tells him, “Happy Valentine’s Day. I love you” – one of the series’ most stirring proclamations of filial love.

“A Day’s Work” is set on Valentine’s Day, 1969, and even as Don is on the upward path, we see Peggy simmering in the hole of resentment into which Don threw her in season six. Peggy has become as Don was, and now it is Don who must help her to ascend. In “The Strategy,” Don and Peggy open up to each other about their shared fears and regrets. “I worry about a lot of things,” Don says, “But I don’t worry about you.” “What do you have to worry about?” Peggy asks. “That I never did anything,” Don replies. “That I don’t have anyone.”

“The Strategy” ends on one of the most beautiful images Mad Men has ever given us – Don, Peggy, and Pete at a dinner table in a Burger Chef restaurant, a surrogate family unit brought together by honesty and authentic connection. This is what utopia looks like:

Intimacy vs. Independence: Divine Comedy vs. American Dream

Ultimately, Mad Men suggests that true happiness is found in moments of intimacy and honesty – a far cry from the image-driven culture perpetuated by the advertising industry, and from the American ideals of individualism and independence. In “The Wheel,” the finale of the first season, Don gave the now-famous Carousel pitch to Kodak – a brief glimpse into what, deep down, we all really want: to be loved.

“Nostalgia literally means ‘the pain from an old wound.’ It’s a twinge in your heart, far more powerful than memory alone. This device isn’t a space ship, it’s a time machine. It goes backwards, forwards. It takes us to a place where we ache to go again. It’s not called a wheel. It’s called a carousel. It lets us travel the way a child travels. Round and round and back home again – to a place where we know we are loved.”

Moreover, this kind of honesty necessarily involves looking back at one’s past – a notion antithetical to the kind of blind, relentless progress that Don so often embodies. Yet “Waterloo,” the mid-season finale of season seven, brings these seemingly conflicting ideas into harmony. The moon landing, the ultimate symbol of human progress, brings people together, as virtually all the characters gather around their television sets, united for a brief moment in collective awe. Peggy capitalizes on this in her pitch to Burger Chef the next day, which centers on the idea of connection.

“Now, I don’t need to charge you for a research report that tells you that most television sets are not more than six feet away from the dinner table. And that dinner table is your battlefield and your prize. This is the home your customers really live in. This is your dinner table. Dad likes Sinatra, son likes The Rolling Stones. The TV’s always on, Vietnam playing in the background. The news wins every night. And you’re starving. And not just for dinner. What if there was another table, where everybody gets what they want when they want it? It’s bright and clean, and there’s no laundry, no telephone, and no TV. And we can have the connection that we’re hungry for. There may be chaos at home, but there’s family supper at Burger Chef.”

“Waterloo” ends with a bittersweet send-off for Bert Cooper, who passes away during the moon landing. His death triggers some infighting among the company, but also brings Ted back to California, and Don unequivocally back into the fold. Mortality can both drive people apart and bring them back together. As Don returns to his office, Bert appears, a messenger from the afterlife, and Don watches, teary-eyed, as he sings:

“The stars in the sky

The moon on high

They’re great for you and me

Because they’re free

The moon belongs to everyone

The best things in life are free

The stars belong to everyone

They gleam there for you and me

The flowers in spring

The robins that sing

The sunbeams that shine

They’re yours, they’re mine

And love can come to everyone

The best things in life are free

The moon belongs to everyone

The best things in life are free.”

As Mad Men enters its final season, there are many paths Don Draper might follow. Perhaps he’ll attempt to drown himself in hedonism, or to run away again, becoming, as some fans have theorized, air hijacker D.B. Cooper. Or perhaps, we can hope, he’ll be able to grasp the happiness that comes from being known and loved – to find, as Dante put it, “the Love which turns the sun and the other stars.”

In “The Mountain King,” the penultimate episode of season two, Don visits Anna Draper (Melinda Page Hamilton), the widow of the real Don Draper, who tells him, “The only thing keeping you from being happy is the belief that you’re alone.” Pointing to a tarot card on her table, Don remarks, “That can’t be good.”

“It is,” she says.

“It’s the end of the world,” Don says in disbelief. She corrects him:

“It’s the resurrection.”