Microsoft’s Best (and Weirdest) Windows Commercials

Windows 10 is coming. Haven’t you heard? Then let these babies tell you. As Redmond’s latest TV spot explains, babies will never know a world without Windows 10, and can smear their fingerprints on computer screens, tablets, and phones without a care.

In the way that Windows is the stolid, almost inevitable operating system for so many, Windows commercials can be a bit predictable. In some ways, that’s not Microsoft’s fault. When it was ready to release Windows 1.0, the world has already seen Apple’s 1984 ad for the Macintosh usher in a new world a year earlier. Beaten to the punch by Steve Jobs, Microsoft execs probably felt like screaming. Which was exactly what Steve Ballmer did all through the Windows 1.0 commercial.

There is a stark difference between how Macs and PCs are advertised, as evidenced by the Mac vs. PC ads staring Justin Long and John Hodgman. But after 30 years of selling operating systems, Microsoft has had a few hits among its misses.

We found 12 commercials for Windows 1.0 through 8. Some of them we could do without, some we can’t get enough of, and others left us confused. Check them out in the slideshow for a trip down memory lane before Windows 10 arrives to enchant a generation of children on July 29.


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