3. John C. Dvorak (http://www.dvorak.org/blog/)
As hoary old sacred cows go, none are closer to "downer" cattle than the venerable John C. Dvorak, who has been expounding on computers since before computers were invented. Dvorak's official bio claims that the man has written more than 4000 articles, a number that seems small in view of his omnipresence.
Beneath those millions of words, Dvorak has buried just about every company and product in the industry, often (nay, usually) with wild prematurity. He famously declared the iPhone a disaster months before Apple released it; and more recently he pronounced Windows 7 to be a total mess, using a forced march of 1000 words to redeploy his argument from a comparison of Windows 7 to OS/2 to a diatribe against the Windows Registry. It's bad enough that people keep giving Dvorak outlets to complain in print, but he also somehow keeps persuading people to put him on TV--or at least on Web video. His most noteworthy video endeavor is Cranky Geeks, a show in which Dvorak invites three tech experts (I've appeared twice) to talk about current events in the industry, and then cuts them off and repeatedly changes the subject to something completely irrelevant and boring. Also: He had nothing at all to do with the Dvorak keyboard.
4. Jason Calacanis (http://calacanis.com/)
Jason Calacanis is to Nick Denton as Donald Trump is to Warren Buffett. A serial entrepreneur, Calacanis has made a living off of building smallish, dot-commy businesses and then selling them off to outfits with much less business savvy. His biggest hit: Selling Weblogs, Inc. (home of the mega-tech site Engadget) to America Online, reportedly for more than $25 million. His latest play: Mahalo.com, a human-powered search engine that seems to have dedicated itself to the goal of beating Wikipedia to the top of the list on a variety of common Google search-term results.
Of course, Calacanis isn't happy just to run these various businesses. He likes to crow about his achievements on his blog, on Twitter, on Facebook, on Flickr...everywhere. A master of self-promotion, Calacanis rarely lets a day go by without plugging something that's under his thumb--and if he has nothing to say about Mahalo, he'll blog about whatever else comes to mind. Recent posts have included scans of childhood photos, a weather report, and--a Calacanis trademark--videos of his pet bulldogs.