From a guy renting his chest for advertising to the Turkish man who may have inspired Ali G’s creator, these websites have a lot to answer for.

The 25 worst websites

PCworld.ca brings you a countdown of the 25 websites that have managed to swindle us out of our money, enslave our computers and hold the net hostage with endless spam, pop up screens and teenage-on-a-rampage web design.

People say hindsight is 20/20. When it comes to the web, hindsight is more like X-ray vision: in retrospect, it’s easy to see what was wrong with dot coms that tried to make a business out of giving stuff away for free (but making it up later in volume) or to make fun of venture capitalists who handed millions to budding web titans who had never run a lemonade stand before, let alone an enterprise.

In fact, it’s so easy we can’t help doing it ourselves. So, as venture capitalists scramble to throw money at anything labelled Ajax or Web 2.0 and web publishing becomes so simple that anyone with a working mouse hand can put up a site, we offer our list of the 25 worst websites of all time.

Many of our bottom 25 date from the dot-com boom, when no bad idea went unfunded. Some sites were outright scams — at least two of our featured net entrepreneurs spent some time in the pokey. Others are just examples of bad design, or sites that got a little too careless with users’ information or tried to demand far too much personal data for too little benefit.

And, to prove we’re not afraid to pick on somebody much bigger than us, our pick for the worst website may be the hottest cyber spot on the planet right now.

So, without any further prelude, here are our “top” picks for worst websites in descending order – with some interesting and sometimes downright weird factoids about each one.

25. Rentmychest.com Look up the word hunk in any dictionary and you will not find a picture of a bare-chested Chris Pirillo, the guy behind download sites such as lockergnome.com. But, you used to be able to find several such pictures at this site, where the pasty, paunchy Pirillo auctioned off messages, written on his chest with magic marker, for $20 a pop. These days the marker-based messages are gone, replaced by a single background image that I wish I hadn’t seen and a bunch of linked keywords. Believe it or not, the keywords are actually more expensive, starting at $200. Look, Chris may know his downloads, but please, somebody buy this man a gym membership.

24. IKissYou.org For a brief period in 1999, an accordion-playing Turk named Mahir Cagri was the most famous man on the net, which really says more about us than it does about this mostly harmless web destination. His site, which featured personal photos, charmingly fractured English and the phrase “Welcome to my home page…I Kiss You!!!”, became a minor web sensation, for reasons that are now entirely obscure. Mahir’s legacy lives on in Sacha Baron Cohen’s (known for his Ali G skit) “Borat” character, who bears more than a passing resemblance to the Turk.

23. InmatesForYou.com This site helps you find that special someone, even if you have to wait 13 years for her parole to come up.

22. Digital Entertainment Network (den.com) This DEN of iniquity blew through more than $100 million before it shuttered its doors in January 2002. A sex scandal involving the site’s CEO didn’t help matters.

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. Hotmail.com 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. 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.

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

13. Whitehouse.com Not the virtual home of the American president (that’s Whitehouse.gov) Whitehouse.com

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