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The 25 Worst Web Sites

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.

Worst Sites #25-#21

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

Click to view full-size image.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.

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