Characters We Hate To Love: Don Draper And Holly Golightly

“Mad Men” came to a close last week, and since then we’ve all been trying to make sense of what the finale meant for the show’s divisive main character. The trajectory of Don Draper’s professional and emotional life has been at times painful to follow, as he’s abused and exploited the people—particularly the women—around him time and time again, coming close to something like redemption but always falling short, always falling back to his shady and selfish ways. And I think the finale keeps up that pattern, even comes full circle on it—he gets right up to the verge of something like redemption, but turns back.

For all his complexities, Don is essentially a static character. And this, I think, is true even if you (still, despite what Showrunner Matthew Weiner had to say about it) want to read the ending more “optimistically,” believing that Don sheds his former self and finds peace. Whether you imagine Don going back to McCann with the Coca-Cola “Hilltop” ad or staying in California, leaving behind the life he had and the people who needed him, he’s doing something he’s done before. The Don who commodifies love to make great ads and the Don who bails, who discards and picks up identities at will, are both entirely on-brand. The difference, in either scenario, is that now he seems to have made peace with it. But here’s the thing that’s still worth noting: he’s made peace with being an asshole, whether that brand of asshole happens to be shameless, culturally-appropriating ad-man or irresponsible, culturally-appropriating pseudo-hippie.

I will be the first to say that Don Draper is not only a frustrating, unsympathetic character but also, a lot of the time, a pretty boring one. But—as a friend insisted to me recently in a loud and lengthy bar debate—you still root for him, don’t you?

And somehow, against my instincts, against my better judgement, against my own repeated arguments for his villainy, it’s true. I still stuck with the show until the very end, and yes—though begrudgingly, and only in small increments—I still root for him.

The anti-hero is an archetype as old as time, but the case of Don Draper is something a little different. He is not a character that audiences love to hate but instead a character that we hate to love, that we invest in in spite of ourselves. I scold myself when I smile at something that goes well for Draper; and yet I can’t help but smile anyway. Even within his fictional world, people hate to love him—but love him they do.

Don Draper is an alpha male. He’s a “man of his time.” He’s the picture of american masculinity. When character descriptions like this abound, it’s easy to construct the irresistible mythos of Don Draper as a sexist double-standard. And, since there are sexist double-standards in just about everything, I don’t doubt that that’s true here—but I do doubt that that’s the whole of it.

Bear with me if this seems strange, but in attempt to make sense of the paradoxically predictable enigma that is Don Draper and our cultural canonization of him, I want to turn to an equally iconic and equally insufferable character from our famed film and television history—a female one, glorified in her femininity perhaps as much as Don in his masculinity: the unforgettable Holly Golightly, as played by Audrey Hepburn in Blake Edwards’ 1961 film “Breakfast at Tiffany’s.”

There are some surface similarities to start with: in both cases we’re situated among the wealthy elite in mid-twentieth-century New York City (the film “Breakfast at Tiffany’s” takes place around the late ‘50s/early ‘60s, though the year is not exactly specified; Mad Men spans the course of the ‘60s), and in both cases, our protagonists don’t really belong there. Just as Don Draper is really Dick Whitman from rural Pennsylvania, Holly Golightly is really Lulamae Barnes from Tulip, Texas. The characters are constructed similarly, by their writers and by their former selves. Each has run away from a life they didn’t want—and a spouse they couldn’t stay with—to recreate themselves with a new identity in the big city. And they have recreated themselves splendidly: though Don has achieved financial success and stability while Holly flounders, relying on money from men she goes on dates with, both are shrouded in charm and glamour. Both firmly believe you can buy happiness, and both make the viewer want to put on their fanciest outfit and smoke a cigarette.

Most importantly, though, both are total assholes. Both are selfish, at least mildly prejudiced, and at times hard to watch. And both are hugely iconic.

For every girl who idolizes Holly Golightly, there is a man who idolizes Don Draper. Which begs a few questions—most obviously, what do we see in them? Why are we so willing to overlook their glaring flaws and to etch them into our cultural memory as role models? If there is something comforting in a flawed hero, fine—maybe we share some of their flaws. But why should we raise up the worst versions of ourselves? Don cheats on his wives like he needs infidelity to breath. Holly uses men for money, and worse, she throws her poor unnamed cat out in the rain. Both intrude on others’ lives constantly but demand aggressively their own privacy, and neither are very good neighbors.

We laud them for being irresistibly charming—but what does that suggest or reinforce about our understanding of charm, of who gets to be charming? Secret impoverished backgrounds don’t wipe away privilege—would Don or Holly really be able to rise from rags to riches so easily if they didn’t happen to be conventionally good-looking white people? Neither character can be removed from the actor that plays them, that lends them so much of what we call their charm.

Holly, too, is a static character, for all her quirky inconsistencies. The Hollywood ending hints at redemption, but when that so-called redemption is nothing more than a kiss in the rain from a handsome man (and, thankfully, a rescuing of the totally abused cat), can we really have much faith in our heroine’s personal growth? As Don returns to advertising, Holly returns to romantic relationships.

There is ample debate on what Holly Golightly means for the American woman, as their is from Draper and the American man. In some ways, her femaleness makes her self-invention and self-centeredness inherently more subversive than Don’s—but it doesn’t make her a feminist hero, and it shouldn’t excuse her ultimately dickish behavior. Holly is cruel to her friends and crueler to her cat, she spouts ignorance and she shirks responsibilities. She is massively frustrating, and it’s hard to feel like she really deserves to come out on top.

And yet—you still root for her, don’t you?

Sara Iacovelli
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