50 Best 'Mad Men' Characters

From one-off cameos to Sterling-Cooper's core players, we're ranking the show's most memorable characters

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Shirley
50
AMC41/50

41. Shirley

Showcase Episode: "A Day's Work"
Loads of women at the Sterling Cooper office excel at making so-over-this-bullshit faces, but few can match Shirley. Especially when she gets her bouquet of roses stolen by Peggy: "I'm getting her coffee and I'm taking my time." She gives notice to Roger with a hilariously sincere attempt at a compliment: "You're very amusing." That one stings, and make no mistake, it was meant to.

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