August 26, 1991: In their first joint interview, Steve Jobs and Bill Gates trade barbs and debate “the future of the PC” in Fortune magazine.
The spirited discussion marks 10 years since the first IBM PC shipped. The piece also looks at what the future holds for both men — described as the former “boy wonders of computing, now thirtysomething.”
August 21, 2008: Microsoft recruits comedian Jerry Seinfeld for a series of ads. It’s a naked attempt to shake the company’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 over the years, 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 Cupertino and its claims that Windows unlawfully copies 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 the company’s 1990s decline.
August 6, 1997: In one of the most famous moments in Apple history, Steve Jobs reveals that Microsoft invested $150 million in its rival.
Although often presented as an inexplicable gesture of good faith on the part of Microsoft boss Bill Gates, the cash infusion into Apple actually benefits both companies.
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.
June 25, 1985: Microsoft co-founder Bill Gates sends a memo to Apple execs suggesting that Cupertino should license its Mac operating system and additional technology to other companies.
Apple CEO John Sculley and Macintosh boss Jean Louis Gassée ignore the advice of the 30-year-old Gates, who at the time is best known as a Mac developer. Five months later, Microsoft releases Windows 1.0.
May 26, 2010: In a massive milestone, Apple passes Microsoft to become the world’s most valuable technology company.
The changing of the guard proves particularly amazing given that, just 15 years earlier, Apple looked close to dead, while Microsoft dominated the tech world thanks to Windows.
May 12, 2005: Longtime Apple frenemy Bill Gates tells a German newspaper that Apple may have hit it big with the iPod, but that its success isn’t going to last forever.
The reason? Mobile phones are going to steal the iPod’s market share. The good news for Gates is that he was right on the money. The bad news for Microsoft is that Apple cannibalized itself by making the iPhone. And Apple’s smartphone became even more successful than the iPod.
April 4, 1975: Childhood friends Bill Gates and Paul Allen found Microsoft Corporation, a software company destined to become a tech behemoth — and a major Apple frenemy.
A few years later, Microsoft will break through to the mainstream with Excel and Word, becoming a key developer of Macintosh software. Then comes the Windows operating system, looking suspiciously Apple-like. After Windows arrives, Microsoft and Apple will embark upon a long-running feud.
March 17, 1988: Apple sues Microsoft for allegedly stealing 189 different elements of its Macintosh operating system to create Windows 2.0.
The incident, which causes a deep rift between Apple and one of its top developers, paves the way for an epic battle between the two companies that will rage for years.
