Windows 2.0 borrowed several elements from the Mac user interface. Photo illustration: Ste Smith/Cult of Mac
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.
Bill Gates' rivalry with Steve Jobs was legendary. Photo: Fulvio Obregon
January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates steps down from his role as Microsoft CEO, a month after his company’s stock hits its all-time high.
The news coincides with a turning point in the long-running battle between the two tech powerhouses. Microsoft begins a long decline from its previous dominance, while Apple continues its rise to the top.
Bill Gates offered high praise for the Mac in 1984. Image: Fulvio Obregon
November 26, 1984: “The next generation of interesting software will be done on the Macintosh, not the IBM PC,” claims Microsoft co-founder Bill Gates in a BusinessWeek cover story.
The claim would seem almost unthinkable coming out of Gates’ mouth just a few years later. But it lands at a time when Microsoft is best known as one of the biggest Mac developers.
One of the most damaging deals in Apple history. Photo: Ste Smith/Cult of Mac
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.”
In a rare joint interview from 1991, Steve Jobs and Bill Gates discuss the "future of the PC" in Forbes magazine. Photo: Cult of Mac (stock image from Reviewsapex)
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.”
"What's the deal with bad advertising?" Photo: Microsoft
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.
A judge's decision proves very damaging to Apple. Image: Ste Smith/Cult of Mac
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.
Bill Gates looking like the cat that got the cream. Photo: Apple
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.