The 25 Worst Web Sites

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Worst Sites #20-#16

20. Hotmail.com

In the mid to late nineties, Hotmail was a virtual Switzerland for spammers, who operated with impunity across the free e-mail service. Hotmail account holders were routinely buried in a blizzard of junk--in part because new subscribers were automatically added to a public directory of e-mail addresses, making them easy pickings for spam harvesters. A massive "dictionary attack" on the site's user base in August 2002 didn't help matters. Later that year Microsoft finally began implementing serious antispam measures, but by then many subscribers had already had their fill of canned luncheon meat.

19. WebVan

The big daddy of dot bombs, WebVan ripped through $1.2 billion of investment capital before checking out for the final time in July 2001. The costs of building a national network of grocery distribution centers proved too great for the online grocer. It's a classic example of a great idea without a viable business model. The only reason it's not higher on our list is that its delivery service was actually pretty good, while it lasted.

18. Beenz.com and Flooz.com (tie)

These ambitious schemes to float a Web-based e-currency both sank like a rock in August 2001. The sites hoped wary Netizens would rather trade credits for goods online than use credit cards, but consumers said No Sale. The biggest difference between the two? Flooz featured Whoopi Goldberg as spokesperson. Her career hasn't been the same since, either.

17. Boo.com

This symbol of dot-com excess burned through cash so fast you'd think its executives worked for the federal government. The fashion retail site featured a 3D avatar named Miss Boo, but the real stars of Boo were its founders, who spent money like it was going out of style--$120 million in six months on lavish apartments and expensive gifts, as well as a site that was too unwieldy for the largely dial-up world of 2000. Amazingly, Boo.com is scheduled for a comeback later this year under new owners. Be afraid, be very afraid.

16. Microsoft Windows Update

Microsoft could have escaped our notice if we didn't have to visit this cryptic and difficult-to-use site so often. It's the only reason to ever use Internet Explorer--and then simply because Microsoft's update site won't work with any other browser. But it's not reason enough.