19. Jerry Seinfeld for Microsoft
What's the deal with that Microsoft-Seinfeld ad campaign? Jerry Seinfeld's short-lived run as master of Microsoft's domain left most of the world in a state of confusion. The commercials, fittingly, were more or less about nothing: One spot featured Seinfeld and Bill Gates shopping for shoes and eating churros; another saw the dynamic duo having an awkward dinner with a random family.
Amid heavy criticism, the Seinfeld era abruptly ended after those two ads -- proving, once and for all, that Microsoft is a bad breaker-upper.
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