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It was so much fun reading the "101 Dumbest Momenets in Business" at Business 2.0's website. Some of the very cool stuff that relate to IT are:

#5
For more nostalgia, you can always check out your legal bills from the DOJ antitrust lawsuit.
"Microsoft has had competitors in the past. It's a good thing we have museums to document this stuff."—Bill Gates, in a talk at the Computer History Museum in Mountain View, Calif.

#7-9
If you can't beat 'em, join 'em.
In April, RealNetworks CEO Rob Glaser—seeing his online music store struggling to compete with Apple's iTunes because it's not compatible with the iPod—e-mails Steve Jobs suggesting that he open the iPod to other purveyors of digital music. The e-mail is immediately leaked to the New York Times, which interviews a surprised Glaser. "Steve is showing a high level of fear," he says.

If you can't beat 'em, and you can't join 'em, encourage people to whine about 'em.Still peeved that Apple won't allow the iPod to play downloads from his online music store, Glaser launches an online petition urging Apple to open up. He quickly pulls the petition offline when he discovers that most of the signers have left strident pro-Apple comments.

If you can't beat 'em, and you can't join 'em, and you can't get people to whine about 'em...put out some half-baked software that forever alienates potential customers?Not backing down, Glaser offers a software hack that allows iPods to play songs purchased from Real. Apple blasts its rival for exhibiting "the ethics of a hacker" and warns iPod users that future updates to its software will render the Real songs unplayable. But it turns out that if Real is acting like a hacker, it's not a particularly talented one: Several Real customers report that the software fills their screens with ads and crashes their computers. In November an Apple software update blocks the hack.