Today in Apple history: Apple fan Jerry Seinfeld joins the dark side

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Microsoft ad
"What's the deal with bad advertising?"
Photo: Microsoft

August 21: Today in Apple history: Jerry Seinfeld appears in failed Microsoft ads 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.

Today in Apple history: Tide turns against Apple in war with Microsoft

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Mac vs. PC
A judge's decision proves very damaging to Apple.
Image: Ste Smith/Cult of Mac

August 14: Today in Apple history: Tide turns against Apple in war with Microsoft 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.

Today in Apple history: Microsoft throws Apple a $150 million lifeline

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Bill Gates
Bill Gates looking like the cat that got the cream.
Photo: Apple

August 6: Today in Apple history: Microsoft investment helps save Apple from doom 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.

Today in Apple history: Windows scores big victory over Mac

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Windows used a number of elements of the Mac UI
Windows used a number of elements of the Mac UI.
Photo: Ste Smith/Cult of Mac

July 25: Today in Apple history: Windows scores big legal victory over Mac when judge throws out Apple's copyright infringement claims 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.

Bill Gates: Steve Jobs was a wizard, but I was immune to his spells

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Steve Jobs Macworld autograph
Steve Jobs (possibly) writing an incantation.
Photo: RR Auction

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.

Today in Apple history: Bill Gates urges Apple to license Mac OS

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Bill Gates
Bill Gates took this strategy and made himself a multibillionaire.
Photo: Fulvio Obregon

June 25: Today in Apple history: Bill Gates urges Apple to license Mac OS 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.

Bill Gates calls failure to challenge iOS his ‘greatest mistake’

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Microsoft should have been Apple's biggest mobile challenger, Bill Gates says.
Microsoft should have been Apple's biggest mobile challenger, Bill Gates says.
Photo: Statsministerens kontor/Flickr CC

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.

Today in Apple history: Apple becomes world’s most valuable tech company

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money
It was a big day for Apple!
Photo: Ste Smith/Cult of Mac/401Calculator

May 26: Today in Apple history: Apple worth more than Microsoft for first time 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.

Today in Apple history: Bill Gates predicts doom for Apple’s biggest product

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Bill-Gates-60-Minutes
Unfortunately for Gates, Steve Jobs was one step ahead.
Photo: 60 Minutes

May 12: Today in Apple history: Bill Gates predicts doom for iPod, Apple's biggest product 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.

Producer of canceled Steve Jobs musical faces $6 million lawsuit

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walt-mossberg-steve-jobs
Musical would have told the story of Steve Jobs and Bill Gates' rivalry.
Photo: Joi Ito/Flickr CC

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.