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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Jim Cutler
Michael Yarish/AMC44/50

44. Jim Cutler

Showcase Episode: "Waterloo"
Okay, so that Cutler, Gleeson & Chaough merger didn't quite work out. But it did bring a splendid new villain into Don's life: Harry Hamlin's Jim Cutler, who looks down on everyone through his giant Barry Goldwater glasses. He tries to squeeze Don out, with a lot of help from Don's liquor cabinet, in favor of budding cartoonist Lou Avery. His motto: "Unless this works, I'm against it."

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