While it's true that the cheesy Steve Ballmer Windows video had bad music, bad hair, and bad acting, it's also true that all that cheese was intentional.
That video was produced for and shown at the Company Meeting, back when a mainstay of the Company Meeting was spoofs of popular television advertisements—what today would be called "virally popular"—with Bill Gates and other senior executives taking the starring roles. The "Crazy Steve" video was a spoof of late-night television advertisements, the most direct influence being the popular-at-the-time Crazy Eddie commercials.
So enjoy the "Crazy Steve" video, but don't fool yourself into thinking this was a real commercial.
Bonus commercial chatter: I don't know the story behind the commercial produced by crack-smoking monkeys. It was shot in one of the Microsoft old-campus buildings, but I don't recognize any of the actors. This leaves open the horrific possibility that the advertisement was for real!
Extra bonus chatter: The original Windows XP commercial, featuring Madonna's Ray of Light, had to be abandoned less than two months before launch thanks to the events of September 11, 2001: A commercial featuring people flying was deemed to be in bad taste so soon after the event. I don't know how they did it, but the marketing department managed to put together a new ad campaign in less than two months. (This also explains why some online ads for Windows XP employed the song Ray of Light, even though the song had nothing to do with the new Windows XP ad campaign: They were leftovers which could be salvaged because they didn't depict flying.)
Too bad, because I liked the original campaign.
Double secret bonus chatter: Could this be proto-Kylie?
Update: an article which includes another story about the filming of the spoof commercial.