"Who is Don Draper?" It was the question that opened the current season of Mad Men, and the question fans of the show had been asking for several years. Unfortunately, some months and 12 aired episodes later, we're coming close to an answer. Don Draper, it would appear, is a pretty bad person. This has, in turn, created an even more puzzling question: Is there any possible resolution that could make us care about him again?
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What's less clear, however, is whether we're ever meant to stop disliking him long enough to care what happens next. Every marginally admirable improvement he's made this season—cutting down to only a few drinks per day, finding a smart, successful lady friend, looking very cool whilst smoking and allowing the soundtrack to play the Rolling Stones' "Satisfaction"—has been undercut by one more hideous failure . The lady friend is neither smart nor successful enough to keep him from sleeping with yet another secretary; the journal where he keeps his sober introspection is (literally) tossed the second he sees a chance to endanger his company's future in the New York Times. Even when he's not actively working to ruin his life and the lives of others, there is the problem of his secret identity. Thus far, Betty has had to lie to the government about it, and Pete has had to turn away business to keep it safe. Knowing the real Don Draper requires you to cover for him, no matter how dangerous, illegal, or costly those lies might be.
And so, here we are, at the bottom of the season. His agency's most important client has dropped him, his career may be about to collapse, and he's pulled a ridiculously risky Hail Mary move that might also be ridiculously stupid. Last time we saw Don in such terrible peril was... well, it was at the end of last season, when he was in the midst of a divorce, his firm was being sold, and his soon-to-be-ex-wife had discovered his secret identity. Don's life tends to develop several all-but-insurmountable obstacles at this time of year.
Last year, however, Don concocted a clever scheme to save his company, salvaged all of his non-marital relationships with charming and heartfelt speeches, and swaggered off to a jaunty tune, ready to begin a new life. It turned out to be his current, extremely depressing life, of course, but that hardly mattered at the time. It was moving; it worked. Because we were rooting for him. No matter what he'd done, we wanted Don Draper to get a win.
This time around, even if Don wins, it will feel hollow. The character appears to have reached the point of no return; we've seen the man commit so many acts of thoughtless cruelty, and wreck his own chances at happiness so many times, that watching the character actually feels like knowing a reckless drunk. Even if he comes through and saves the day this time, he's going to ruin it all again tomorrow; what's the point of hoping?
But then, the other option is to let him fail, and fail in an exceptionally humiliating and gruesome way which will carry severe, terrible consequences for every character on the show. That's entirely plausible, of course. "Exceptionally humiliating and gruesome" just so happens to be a major part of the show's tonal palette, and "severe, terrible consequences" are its favorite form of plot twist. But if the show does this, a large part of the audience will feel cheated, and they'll have every right to feel that way. The show has already gotten very dark this season, and if it ends without bringing us even a little hope, it may be hard to invest anything in it emotionally. Mad Men is a great show put together by talented people, but Formerly Mad Men Living In Cardboard Boxes Under The Subway Tracks As Defeated Shadows of Their Former Mad Selves just doesn't have a lot of appeal, premise-wise.
Of course, the most fun of guessing the outcome of the finale is precisely this; either Don will score a hollow victory, or the show will crush us with his entirely realistic defeat. But either way, it will be at least a little terrible. It should be. Mad Men has become one of our most popular tools for talking about white, straight male privilege in America; it's all but allegorical in its treatment of it. And both potential resolutions to the problem of Don are satisfying as allegory. No matter how much resistance that privilege meets, it tends to find a way to preserve itself, and to maintain control of the world around it, like Don. No matter how powerful that privilege is, it's always being met with resistance, also like Don. The particular lifestyle and form of wealthy, corporate masculinity that Don represents came to an end in the '60s: Don loses. Masculinity, corporations, and wealth themselves only change their shapes a bit, and ultimately survive: Don wins. Both are true. Both are going to happen.
At this point, the show has committed itself to telling the same story in many different ways, many times over. It's the same story they've been telling us all along, if you hadn't noticed: A man's whole world falls apart, and he falls with it. He goes down and down, until it seems the fall will kill him. Then he lands, in the same way every time, impossibly safe once more. He lands safely, so that we can watch him fall again.
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