The 11 Stupidest Moments in Tech for 2008

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A Wikipedia Love Story

In a classic case of mixing business with displeasure, Wikipedia cofounder Jimmy Wales dumped his girlfriend, ex-Fox commentator babe Rachel Marsden, and posted the news on Wikipedia. In retaliation, Marsden put some of Wales's clothing (left at her apartment in New York) up for auction on eBay and said some snarky things about Wales in the process. Anyway, Valleywag, the tech industry's equivalent of the National Enquirer----broke the whole story and even unearthed some of the steamy IM conversations between Wales and Marsden.

Here's our favorite line from the Valleywag coverage: "Marsden subsequently told friends that Wales gave her feedback on her website design - is that what kids are calling it these days? - for 24 hours straight in a D.C. hotel." It took me about an hour to figure out what actually happened in the tragicomic affair, and I felt about 10 IQ points lighter afterward.

Another Year, Another "Google Killer"

One of the most widely anticipated new products of 2008, a search engine called Cuil, developed by four ex-Google people, was hyped (not surprisingly) as a "Google killer." The new search engine debuted, kinda sucked, and then sorta disappeared.

The first mystery was how to pronounce the product's weird name (like "cool," not "quill" or "kewl" or "cue-ill"); the second puzzle was what the name meant (allegedly an old Irish term for both "knowledge" and "hazel"), and the third and biggest stumper was why Cuil's search results had such a weak relevance quotient, to the point of being bizarre. Some first-time users reported that Cuil even had trouble yielding relevant results when searching its own name. That's just nuts.

Microsoft and Yahoo: Will They or Won't They?

Will Microsoft buy Yahoo? The behemoth of Redmond launched an unsolicited $44.6 billion takeover attempt of the venerable Web portal this year, an effort highlighted by a personal love note from Microsoft CEO Steve Ballmer to the Yahoo board. Then Yahoo, which could really use a date, played hard to get for so long that Microsoft gave up, never to return. Well, not in 2008, anyway.

The failed courtship generated no small measure of frustration among Yahoo investors. Here's billionaire investor Carl Icahn in a letter to the Yahoo board of directors:

"Until now I naively believed that self-destructive doomsday machines were fictional devices found only in James Bond movies. I never believed that anyone would actually create and activate one in real life. I guess I never knew about [Jerry] Yang and the Yahoo Board."

Was Yahoo leader Jerry Yang the man who botched the deal? A lot of people think so. Maybe Yang did, too. He stepped down as Yahoo CEO in November.

Sprint: What If Roadies Ran the World?

It's funny how the advertising industry has conditioned us not to expect to find any connection between the subject matter of ads and the products they promote. My favorite example this year (other than this one from Gatorade) was a Sprint commercial that imagined a world in which roadies (the guys that lift the amps and pull the wires for rock bands) run everything--in the ad, an airline. I giggled at the 30-second spot, but it could just as well have been used to pitch fish sticks or odor eaters. Anyway, here it is.

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