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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Jeffrey Graves
Carin Baer/AMC42/50

42. Jeffrey Graves

Another great one-shot. Paul Kinsey's Princeton pal Jeffrey shows up at the Sterling Cooper office to get the crew high, including newbie Peggy Olson. ("My name is Peggy Olson and I want to smoke some marijuana.") They all spend a strange stoned afternoon together, though it gets ugly when Jeffrey taunts Paul about his Jersey roots and his expulsion from the Princeton Tigertones. (Paul is touchy about his vocal skills.) But they reconcile for a bizarrely touching duet on "Hello! Ma Baby," which gets the ultimate rave review from Peggy: "I am so high!"

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