The 25 worst Web sites of all time

21. Golden Palace Casino Websites used to do just about anything to make headlines and Golden Palace’s ad campaigns took that idea just about as far as it could go. From buying the “Holy Toast” — the grilled cheese sandwich that looks like the Virgin Mary — to buying William Shatner’s kidney stone, no promotional gimmick is too cheesy for this online casino.

20. In the mid to late nineties, Hotmail was a virtual Switzerland for spammers, who operated with impunity across the free email 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 email 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 anti-spam 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 network of grocery distribution centres 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. and (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. 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, 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.

15. Are your pets embarrassed about being neutered? Their four-legged friends need never know, thanks to Neuticles — implants that restore the look if not the function of their recently removed body parts. Yes, these cosmetic cojones are no joke. Prices start at US$73 a pair. Not to be confused with BumperNuts, which provide a similar service for your car.

14. Sadly, this site is exactly what it says it is. Think Priceline for face-lifts and tummy tucks. No, we are not joking.

13. Not the virtual home of the American president (that’s began life during the Clinton era as a site devoted to political discourse. In September 1998 it helped distribute the Starr Report, but, by then, it had also become the most notoriously named porn site on the web–featuring, among other things, a White House Intern of the Month. Today the site hosts a white-pages listing.

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