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Pop culture obsessives writing for the pop culture obsessed.

“Both Sides Now” marked the end of Don Draper’s duality

Illustration for article titled “Both Sides Now” marked the end of Don Draper’s duality

In Hear This, A.V. Club writers sing the praises of songs they know well. This week, in honor of the return of Mad Men on April 5 for its final seven episodes, we’re looking at some of the show’s most important song selections.


Judy Collins, “Both Sides Now” (1967)

I’ve seen every episode of Mad Men (many more than once), but none made my jaw actually drop like the season-six finale “In Care Of.” In the middle of a major pitch to Hershey, Don Draper (Jon Hamm) veers from his bullshit story about how his dad bought him a Hershey bar for mowing the lawn, after he tells the room, “the wrapper looked like what was inside.” He has already won the account, but finally fed up with his own constant duality (his wrapper looks nothing like his inside), he realizes that he can lie no longer. So he tells a Dick Whitman story about how, when he was growing up in a whorehouse, the company’s chocolate was the only sweetness he knew:

Closest I got to feeling wanted was from 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.

With this statement, after six full seasons, the curtain completely falls between Don Draper and Dick Whitman, as Don publicly owns up to his beyond-humble upbringing. Unfortunately, the pitch has the opposite effect of Don’s previous home runs like “The Wheel”: Everyone in the room is freaked out, even Don’s own coworkers, who until that point had functioned as his makeshift family. The penalty Don had always feared from revealing himself becomes real, as he is ousted from Sterling Cooper & Partners.

Fortunately, Don realizes he still has a family, one that he hasn’t spent nearly enough time with: his daughter and two sons. So he picks up Sally and the boys and ends the season standing in front of the old whorehouse, telling them, “This is where I grew up.” It’s a life-altering moment for them all, but especially for Sally, who always knew her father was hiding something and longed to know what it was. Now she does, and the two share a careful, thoughtful glance before the season comes to a close.

As soon as Don says his final line, Judy Collins’ version of Joni Mitchell’s “Both Sides Now,” kicks in and continues over the credits. The angelic-voiced Collins epitomized the folk-music movement that was beginning to seep into the mid-’60s. Her version of this song on Mad Men declared that the long Dick/Don separation was over. In the seventh and final season, Don continues to wrestle with work, with marriage, even with his kids, but he no longer has a façade to hide behind: Everything he does now is out in the open. As he fights to get his company position and his family back, he’s finally doing it as no one but himself.

Collins’ version of Mitchell’s song sounds sunny and hopeful, even as the lyrics describe tossing “ice cream castle” fantasies aside in favor of less-pleasant—but far more honest—realities: “It’s life’s illusions I recall / I really don’t know life at all.” The all-important message—on the show and in the song—is that the illusions are finally over.