Remember the Old Rivalry Between Apple & Microsoft? This 2006 Video Will Remind You

Mar 18, 2023 - 3 Comments

Do you remember when Apple and Microsoft had a substantial public rivalry? Apple was the underdog, known for its innovative designs and user-friendly interfaces, while Microsoft was the goliath, better known for widespread adoption and the associated practicality.

This video from WWDC 2006 of Steve Jobs and Bertrand Serlet roasting Windows similarities to Mac OS will certainly refresh your memory of just how sharp that old corporate rivalry was. And in case you were wondering, this is pre-iPhone, back when Apple was still quite an underdog, and their primary product lines were the iPod and the Mac.

Can you imagine a WWDC keynote being anything like that today? There just isn’t the motivation, as there’s seemingly no longer a rivalry between the two companies. In the battle of PC vs Mac, it was the iPhone that won – Microsoft doesn’t even make a Windows phone anymore (regrettably too, the smartphone duopoly could use some competition).

Fun find over at daringfireball, who points out that Bertrand Serlet is now an employee of Microsoft, which still feels like quite a talent loss for Apple.


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Posted by: Jamie Cuevas in Fun


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  1. Rudi says:

    Now Microsoft has copied most of macOS (i.e.Unix & derivates) but the feeling is just something different on Mac.

  2. Steve Steele says:

    The good old days! I’m an old school MacOS user, going back to System 6 and 7, and I’ll always have this rivalry in my blood. The best part of this rivalry is Steve Jobs. The most charismatic CEO or iCEO of all time for sure.

  3. Sebby says:

    Yup. And now Apple are “The iPhone company”, and bears a striking similarity to Microsoft in many ways. They still copy each other, but now to the mutual benefit of maximal profit-seeking at customer expense. Truly, the war is over, and the only real victims are the customers. It’s the legacy of functionality that matters most on desktop, and (what’s left of) privacy on the smartphone. I love Apple’s hardware but I continue to be on the point of going back to Windows for desktop.

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