Hammered by Apple's hugely successful Mac-vs.-PC commercials (starring Justin Long and John Hodgman, respectively, as the embodiment of the different computer systems), Microsoft reportedly paid Jerry Seinfeld $10 million for a series of ads also starring Bill Gates. In the ads, the two appear in a discount-shoe store, where Jerry helps Bill try on a new pair of kicks. It was hard to see the relevance of Seinfeld whose sitcom went off the air in 1998 and Gates, other than the fact that both are so rich that the idea of them discount-shoe-shopping is ridiculous. The tagline for the commercials was "Microsoft. Delicious," which was equally vexing. When it became clear that the public just didn't get whatever joke or message Microsoft was trying to convey, the company admitted in a statement, "The answer, in the classic Seinfeld sense of the word, is nothing." Apparently Microsoft decided the Seinfeld ads didn't quite hit the mark. The commercials were pulled soon after their debut and replaced with an ad campaign directly targeting the Apple ads, in which regular Americans and some celebrities including Eva Longoria and Tony Parker admit, Alcoholics Anonymous style, that they too are PCs. After the switch, Microsoft said the short-lived Seinfeld commercials were all part of their marketing master plan.
Top 10 Microsoft Moments
Windows 7 drops Oct. 22. With programmers everywhere hoping it will be better than Vista, TIME looks back at some of Microsoft's biggest wins and its worst mistakes