The Ugliness of Don Draper

Bhaskar Chawla
6 min readJul 8, 2020

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In an age where a TV show can age badly even in five years, it might be unwise to rewatch an old favourite. However, when I chose to rewatch Mad Men, I was (mostly) vindicated in my belief that the show was ahead of its time and had the capacity to truly withstand the test of cultural growth. This is not to say that there is nothing about the show that rankles in a world where Me Too has completely changed the lens through which we view art and pop culture. But Mad Men remains a stellar piece of Golden Age television because it was, above all, a scathing indictment and close-to-perfect portrayal of toxic masculinity.

During its original run, Mad Men was seen as a critique of capitalism and consumerism and a study of identity set in the decade that changed the Western world and, by virtue of eurocentrism and U.S cultural hegemony, the world. Through its characters and the world of advertising, Mad Men captured the decade that changed the world’s perception of the United States from the last stronghold of cultural conservatism in the West to a liberal society seemingly built on individual freedom. Gender relations was a major theme in Mad Men and the show pulled no punches in its portrayal of rampant and casual misogyny. But what really stood out was how everything about Don Draper from his shadowy past to his character arc was a subtle but very clear exploration of masculinity.

Don Draper’s identity is inextricably tied to his past. His past as Dick Whitman governs Don’s life as an ad-man because most of what he does is in an effort to keep this past hidden from everyone in his present life. His relationship with Anna Draper (the real Don Draper’s wife) and her niece is starkly different from his relationship with those closest to him in his own life. With the latter, he’s always guarded, ever-so-keen to project an image of power and charisma. When Betty finds out who he really is, Don’s veneer of calm comes off completely and he is shocked to his core because he has no control anymore.

Don’s profession and what he does at his job are two other devices through which Mad Men signals what it’s trying to tell us about masculinity. Being an advertising creative is an overt show of Don’s role in creating and perpetuating a culture of duplicity — one where things are made out to be much better than they actually are. How Don is at his job is a far subtler clue as it takes careful viewing and analysis to understand what it symbolises.

In the world he occupies, Don Draper is portrayed as the envy of the advertising world. He is the holy grail of creatives; agencies are always trying to poach him and even acquire Sterling Cooper and its future iterations only to get the great Don Draper to work for them. But through the course of the show Don is shown to be far less able at his job than his peers believe him to be. His primary strength lies not in creating actual ads that work, but charming clients into believing that the ideas he’s pitching to them account for the pulse of the public. Not only that, he specialises in coming up with one-line ideas or tags to wow clients, but rarely does he come up with entire advertisements.

The show drops many clues to tell us that Don isn’t nearly as good at his job than others believe him to be. In a confrontation with his friend and protégée, Peggy, it is revealed that the primary idea for an ad he won an award for was actually conceived by her. His argument is that Peggy’s idea was a kernel, to which she says “Which you changed just enough so that it was yours.” While the argument ends with the takeaway that “this is how advertising works”, it shines a light on what Don does to create the brand of Don Draper.

Later on in the show, ideas presented blind to the team on an account result in everyone preferring the one conceived by Michael Ginsberg, one of Don’s underlings, over his own. Don’s insecurity leads him to leave the artwork for Ginsberg’s idea in the taxi on his way to the pitch. When Ginsberg tells him later that he feels sorry for Don, Don pretends to not care but seems visibly affected later.

Don’s insecurity manifests itself even more once SCDP merges with CGC and he has to work alongside another handsome and charismatic creative director, Ted Chaough. But the glass shattering moment comes in the final season when a copywriter, John Mathis, embarrasses himself at a pitch meeting with a client by fighting with a colleague. Don’s advice to him is to not apologise, because that would make the client lose all respect for him. Instead, Don advises him to make a joke that he once made in a similar situation. The result is disastrous as the client takes offence and demands that Mathis be taken off the account. Mathis barges into Don’s office and tells him that Don’s joke could only work for him because the client he used it with was a closeted gay man infatuated with Don. His parting gift before Don fires him is to say that Don only gets by in life because he’s handsome.

Don’s personal life is a more obvious signifier of fragile and toxic masculinity. He wants the perks of being a family man without the responsibilities. He wants to have affairs but even the slightest threat of being exposed as a philanderer angers him. When he discovers that Betty’s been having an affair, he’s angry not so much because she cheated on him, but because he heard about it from Roger, which meant that the world knew about it. He cannot stand Megan filming intimate scenes on her show because the world can also see it.

Don’s life, just like the lives of other primary male characters on the show, plays out like an eternal quest for “happiness” — to feel how they’ve been conditioned to be entitled to feel. And yet the idea that a woman could also want this happiness is incomprehensible to him. Don is stumped by Betty’s need to see a psychotherapist and, later, angry at her desire for a divorce because in his mind, she got everything she ever wanted with him and cannot possibly want more. A repeat of this is seen when his second wife, Megan, wants to quit advertising and act. For Don, the fact that Megan works is enough to make her happy, regardless of what work it is.

Mad Men’s finale makes it more obvious than anything that the character of Don Draper was designed specifically to critique masculinity. From the three phone calls he makes to Sally, Betty, and Peggy from a retreat in California, Don realises that everything he tried to project about himself was a lie while his worst fears about himself were true. He’s not a “family man”; he barely cares about his children enough to be their guardian. He already knows that he ruined Megan’s best years. At the moment when he’s shattered and dazed, the thing that really resonates with him is a stranger talking about the emptiness of his own life; how he spent his whole life thinking that he’s not getting love because he just doesn’t know what it is. Don’s own life, despite all of its peculiarities, reflects the universal truth of masculinity; it’s a life where the part of you that’s supposed to be vulnerable, that’s supposed to feel, that’s supposed to love, is destroyed so early that one never learns what it is.

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