The puzzle of Mad Men is why many liberal-minded men and women are so fascinated by the character of Don Draper when he appears to be an avatar of patriarchal privilege that left politics traditionally opposes. Does this signal some kind of regression? Or a sign of vestiges of undiscovered elements of sexist ideology hidden in our unconscious liberal minds?
But the problem with interpreting Mad Men in this way is that it should mean that the conservative right, who are often even overtly sexist, should be even more enthusiastic than liberals, as they are for the show 24. Why is this not the case?
Asking “Why do we take Don Draper, a problematic character, to be the apogee of masculinity?” is missing the point, the real question is “Why are we nostalgic for a time when there still was a apogee of masculinity?” The social standards that dictated how a “true” man looked, talked and moved was discarded as conformist, limiting and oppressive. What is or isn’t a true man is up to each individual to decide for himself, not a cultural standard that discriminates against those who are different. Realizing one’s authentic self is the ultimate liberation.
I claim that Don Draper is appealing because he embodies the opposite of this, a liberation from the liberation. Not just because he’s a fake and his real name is Dick Whitman. The whole point is that not only is he kind of a bad guy & not really the ideal man, he’s even more radically a fraud as Dick Whitman. Yet despite that, he still manages to be successful at being Don Draper, even in the eyes of the audience who know the truth.
This is because an ideal is impossible, it can never be achieved. An impossible ideal seems oppressive, you are being held to a standard that you cannot hope to achieve. But on the other hand, because every attempt to realize the ideal is conditioned by failure, it’s understood that no-one ever achieves it. It’s like a Platonic ideal that doesn’t exist in reality - it’s understood that we only ever approximate it, never truly embody it, and that’s OK.
In contrast, the cult of authenticity, which seems to not demand anything or judge us, only asking us to be ourselves, is paradoxically must more oppressive because it claims to represent an achievable goal. Just be who you are. But we can never be unmediated, unselfconscious individuals spontaneously expressing just who we are free of all external influences, it’s also an impossible ideal. Except not being able to achieve it is decidedly not OK. Authenticity can’t be approximated, it must be embodied here and now or it means nothing, otherwise you are just a fraud.
The demand to “be who you are” is much more oppressive. Wanting to be Don Draper is really wanting to live in a more forgiving world, where our failure to live up to a standard still carries with it a certain nobility.