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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Duck Phillips
Carin Baer/AMC31/50

31. Duck Phillips

Showcase Episode: "Three Sundays"
So many ups and downs for the Duck — most of them involving the bottle, as in the drunken rant that gets him dragged out by security at the Clio Awards. (Roger Sterling cracks, "I miss working with that guy.") His pivotal moment: at a secret meeting with the Brits, taking a sad look into his martini glass, right before he takes that fateful sip and makes his pitch to sell Sterling Cooper. Alas, he never could hold his liquor.

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