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 Apple 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 Cupertino’s 1990s decline.
August 6, 1997: In one of the most famous moments in Apple history, Steve Jobs reveals that Microsoft has invested $150 million.
Although often presented as an inexplicable gesture of good faith on the part of Microsoft boss Bill Gates, the cash infusion 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: 30-year-old Bill Gates, at the time best known as a Mac developer, sends a memo to Apple CEO John Sculley and Macintosh boss Jean Louis Gassée.
His suggestion? That Apple licenses its Mac operating system and additional technology to other companies. Apple’s management ignores his advice. Five months later, Windows 1.0 is released.
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, which became even more successful than the iPod.
The co-founder of Microsoft joined the chorus of voices speaking positively about Apple today. Bill Gates’ relationship with Apple goes back to the very dawn of the company, and he and Steve Jobs were the best of frenemies.
Now that he’s a philanthropist rather the CEO of Microsoft he can speak openly about a former rival.
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, with the company becoming a key developer of Macintosh software. Then comes the Windows operating system, looking suspiciously Apple-like. After that, Microsoft and Apple embark upon a long-running feud.
