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25 worst web sites > I June 22, 2007

Posted by grhomeboy in Internet.
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From unforgettable flame-outs to some of the most popular destinations around, no one is safe from our look at the world’s dumbest dot-coms and silliest sites.

 

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.

It’s so easy, in fact, we can’t help doing it ourselves. So as venture capitalists scramble to throw money at anything labeled 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 Web sites 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 Web site may be the hottest cyberspot on the planet right now.

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 “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
Web sites 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 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.

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