23. Duck Phillips, 'Mad Men'
For every Draper, there is an equal and opposite anti-Draper. Not-quite-recovered alcoholic advertising executive Duck Phillips (Mark Moses, in a challenging role) was a recurring thorn in the side of Mad Men's main man, a fact made all the more frustrating by the fact that Don hired him to begin with; he also stood as the single strongest example of Peggy Olsen's terrible taste in men. Whether attempting to shit in Don's office, staging a drunken swing-and-miss brawl with him in the men's room, or (most unforgivably) ditching his family dog, Duck never had his ducks in a row. It didn't make him the office's resident alpha male, but it did make him the perfect foil for Draper's unbeatable combo of looks, lies, luck, and raw talent.