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.
There are plenty of words used to describe Steve Jobs, but “wizard” isn’t one of the ones we hear too often.
That’s exactly what Jobs was, however, according to Microsoft co-founder and long-time Jobs frenemy Bill Gates. Speaking on CNN, Gates said that Jobs accomplished his Apple-correcting wizardry by “casting spells.” But Gates, as a “minor wizard,” was immune to Jobs’ hocus pocus.
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.
Former Microsoft CEO and Steve Jobs frenemy Bill Gates says his company massively missed out by failing to challenge Apple on smartphones.
Describing his “greatest mistake ever,” Gates said the failure to become Apple’s main competitor in the mobile space cost Microsoft $400 billion.
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.
An abandoned 2016 musical about the rivalry between Steve Jobs and frenemy Bill Gates has resulted in the producer being sued for $6 million.
The musical’s producer allegedly told investors he had funding from Microsoft for the project. In fact, the musical was $1 million in debt at the time. It was ultimately canceled just two weeks before it was due to open.
