November 21, 1985: Following Steve Jobs’ departure, Apple comes close to signing its own death warrant by licensing the Macintosh’s look and feel to Microsoft.
The deal, between Microsoft co-founder Bill Gates and Apple CEO John Sculley, comes hot on the heels of the Windows operating system’s release. The pact gives Microsoft a “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs, and to license them to and through third parties for use in their software programs.”
August 21, 2008: Microsoft recruits comedian Jerry Seinfeld to appear in a series of ads. It’s a naked attempt to shake Microsoft’s reputation as a “stodgy oldster” (as opposed to Apple’s trendsetting hipster image).
Microsoft pays Seinfeld a reported $10 million for the ads. However, thanks to the Mac’s appearance in virtually every episode of Seinfeld, the comedian remains the world’s most famous Apple fanboy.
August 14, 1991: As Apple and Microsoft head to court to battle each other, the tide begins to turn against Apple and its claims that Windows has unlawfully copied the look and feel of Mac OS.
The case concerns whether key elements of Apple’s operating system are original enough for copyright protection. The decision turns out to be a major blow against Apple — and the start of Cupertino’s 1990s decline.
July 25, 1989: Apple suffers a major setback in its copyright infringement lawsuit against Microsoft for allegedly stealing the Mac’s “look and feel” to create Windows.
Apple sued Microsoft on 189 counts of copyright infringement relating to Windows 2.0.3. The judge overseeing the case throws out 179 of them. This paves the way for Microsoft’s dominance over Apple in the coming decade.