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.