Microsoft picked up the most points for IT company blunders in an annual rundown of the 101 Dumbest Moments in Business.
The software giant managed six entries in the list, although Yahoo grabbed the top spot for high-tech cock-ups, coming in second overall.
Yahoo was awarded the slot for paying an undisclosed sum to Wylie Gustafson, the yodeller in its ads, after he sued the company for $5m, claiming that he was paid only for limited use.
Brian Valentine, Microsoft's senior vice president for Windows, came in fifth for his gaffe at a conference when he declared that every industry operating system was about equal. "We all suck," he said at the time.
Microsoft also grabbed the number 11 spot, for its aborted attempt at its own 'Switch' ad.
Trying to blunt Apple's 'Switch' campaign, Microsoft posted a page on its website entitled 'Confessions of a Mac to PC Convert', featuring a woman touting Windows XP.
It was quickly revealed that the woman pictured was a model and that her 'confessions' were written by a freelance writer paid by Microsoft.
Redmond was also ranked 41st for promoting its MSN 8 online service with hundreds of butterfly logo decals throughout New York City.
While chief executive Steve Ballmer (48th and 49th) and chairman Bill Gates (50th) garnered spots for explaining .Net again and again and again.
Microsoft rival Sun Microsystems also made the list, but at a lowly 92. During a keynote speech at Comdex 2002, Sun chief Scott McNealy said: "All us CEOs are auditioning for Jackass the Movie: Part 2."
Corporate mishaps from Hewlett Packard, PwC Consulting and Nokia were also highlighted.
Josh Quittner, editor of Business 2.0 magazine, which compiled the list, said: "This past year was chock-full of unusually wacky, not to mention hilarious, gaffes."
The full list can be seen here.
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