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.

Dan Tynan, PC World

Friday, September 15, 2006 05:00 AM PDT

Artwork: Chip Taylor

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 labled 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.

Feel free to start at the bottom and work your way up, or jump ahead and read about the worst of the worst.

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

You'll find a truly captive audience at 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

The Golden Palace Casino site is the place to go for over-the-top ad campaigns...and used kidney stones.

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.

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.

Worst Sites #15-#11

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. In an especially nice touch, the site opens with a flash animation of a bouncing ball (naturally). Yes, these cosmetic cojones are no joke; prices start at $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 our president--that's Whitehouse.gov--Whitehouse.com 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.

12. The Dancing Baby

Both strangely amusing and deeply disturbing, the famous dancing toddler boogied its way across the Internet and into the spotlight, appearing on both Ally McBeal and a Blockbuster video commercial during the mid-nineties. There are now dozens of variations on thousands of sites. If you're looking for the parties responsible for giving birth to this phenomenon, blame its parents at Burning Pixel Productions.

11. Rabies for Kids

Look, kids: Rabies can be fun!

Here's what happens when good intentions meet really bad design. Published by the Viral and Rickettsial Zoonoses Branch of the Centers for Disease Control, the Rabies for Kids site is an orgy of graphical offal. You'll be foaming at the mouth long before you reach the "Activities" section, which features a photo of a dog's brain being sliced with a scalpel.

Worst Sites #10-#6

10. MyLackey.com

This Seattle-based site offered to walk your dog, pick up your dry cleaning, and do all other manner of scut jobs for a fee. (Isn't that what kids and younger siblings are for?) The dot com contracted with local service providers for the dirty work, but apparently applied the "lackey" notion to its own employees as well. An infamous memo from cofounder Brendon Barnicle berated the company's 65 employees for not putting in 11-hour days, making MyLackey a symbol of the dot-com work ethic. Sixteen months after it began, the last lackey still standing closed the doors and shut off the lights.

9. Hamsterdance.com

Quite possibly the most irritating site on earth. Earplugs recommended.

8. BonziBuddy

This animated purple gibbon called itself "your best friend on the Internet," but many who downloaded this free program weren't feeling too friendly afterward. Buddy could tell jokes, recite your e-mail, manage your schedule, download files, and more. But the grape ape also tracked users' surfing habits, hijacked home pages, and installed several of his adware buddies. Depending on your browser settings, merely visiting Bonzi's Web site or clicking a banner ad could install Buddy on your machine. In 2002 annoyed Netizens had enough of this monkey business and sued Bonzi for deceptive advertising. By 2005 Buddy was history.

7. Pets.com

Who let this dog out? Back in the heady days of 1999 it must have seemed perfectly normal to spend $175 million making a sock puppet famous. But the notion of saving some coin on kibbles and kitty litter never caught on with consumers, and by November 2000 Pets.com had been euthanized--going from IPO to liquidation in just nine months. Before it got sent to the pound, however, the dot com filed suit against Triumph the Comic Insult Dog for allegedly defaming its moth-friendly mascot. Apparently, even sock puppets have feelings.

6. Pixelon.com

More dot con than dot com, this streaming media company boasted of a revolutionary new technology that would deliver high-quality audio and video over the Net. But Pixelon CEO and founder "Michael Fenne" was in reality a grifter named David Kim Stanley, who spent the majority of investors' money--some $16 million--on a launch party in Las Vegas featuring Tony Bennett, KISS, and The Who. Prior to starting Pixelon, Stanley had pleaded guilty to swindling friends and neighbors out of $1.5 million; he was on the lam and living out of the back of his car when he founded the company. Pixelon's revolutionary new streaming technology was equally spurious.

Worst Sites #5-#2

5. AllAdvantage

AllAdvantage: Such a deal!

This site had the brilliant idea of paying people 50 cents an hour to surf and watch banner ads all day, plus another 10 cents per hour for every friend they convinced to sign up. All users had to do was install a "Viewbar" that displayed ads and clocked how much time they spent online. Stunningly, the company managed to raise $135 million in venture capital and convince 2 million users to sign up before it folded in February 2001. For some reason, advertisers failed to see any advantage in trying to reach the $4-a-day demographic. Go figure.

4. CD Universe

In December 1999 a Russian hacker named Maxim broke into the music retailer's site, stole 350,000 credit card numbers, and then demanded $100,000 ransom. When CD Universe refused to pay, Maxim posted 25,000 of the numbers to a Web site. At the time CD Universe was owned by eUniverse, which combined its site and its customer database on an unprotected server. "Basically, they put the candy jar in plain sight and left the cover off," says current CD Universe owner Chuck Beilman. "It was only a matter of time until someone stole the candy." CD Universe's customer database is now separate from the Web site, encrypted, and protected by a firewall.

3. Cartoonnetwok.com

No that's not a typo; it's "typosquatting," where a site owner deliberately registers a misspelling of a popular domain in the hopes of attracting the actual site's traffic. Cartoonnetwok was one of some 5500 deceptive domains owned by John Zuccarini, d/b/a/ "Cupcake Confidential." But that wasn't Zuccarini's only nasty bit of business. FTC investigators visiting one of his sites found their screens filled with 29 new browser windows for instant credit, online psychics, gambling, and porn sites. When they hit the Back button, another 7 windows opened--a technique known as "mousetrapping." Worse, many of Zuccarani's typosquatting sites were aimed at children. In 2003 Zuccarini pleaded guilty to violating the Truth in Domain Names Act and was sentenced to 2.5 years in the federal pen.

2. CyberRebate

The phrase "the check's in the mail" took on new meaning with this dot com. CyberRebate offered to refund 100 percent of what you paid for electronic goods, provided you a) paid up to 10 times their normal retail value, and b) let CyberRebate hold onto your money for at least 10 weeks. The site banked on people simply forgetting to apply for the refund. Unfortunately for CyberRebate, not enough of them did. The company filed for bankruptcy in May 2001 owing $60 million in refunds. Aggrieved customers had to settle for roughly 9 cents on the dollar.

Worst Sites #1

1. MySpace.com

Even a MySpace page about Beyonce page looks pretty ugly. I didn't think that was possible.

Yes, we know. With more than 90 million users, MySpace is now more popular than Elvis, "American Idol," and ice cream. But the Web's most visited destination is also its most poorly designed and counterproductive.

The ease with which anyone of any age can create a page, upload photos, share deeply personal details of their lives, and make new "friends" quickly turned MySpace into a one-stop shopping mall for online predators. That in turn has made the site an easy target for politicians who pander for votes by playing on parental fears. In an era when the basic tenets of the Net are under attack by both Ma Bell and Uncle Sam, MySpace is a headache we don't need.

But let's put all that aside for a moment. Graphically, many MySpace pages look like a teenager's bedroom after a tornado--a swirl of clashing backgrounds, boxes stacked inside other boxes, massive photos, and sonic disturbance. Try loading a few of those pages at once and watch what happens to your CPU. Watch out for spyware, too, since it turns out that MySpace has become a popular distribution vector for drive-by downloads and other exploits. And in a place where "U are soooooooo hot!!!" passes for wit, MySpace isn't doing much to elevate the level of social discourse.

In response to a public backlash and some well-publicized lawsuits, MySpace has begun modifying its policies--for example, limiting adults' ability to contact minors. That's hardly enough. Requiring some kind of authentication from MySpacers--or their parents--to validate their ages and identities would go a long way toward scaring off the creeps and making the site a kinder, gentler social network.

Is MySpace totally bad? Not at all. Are we old farts? Yeah, probably. But the Web's most popular site needs a serious security reboot. And probably a makeover. Until then, MySpace won't ever be OurSpace.

Contributing Editor Dan Tynan considers himself the Leonard Pinth-Garnell of high-tech journalism. He writes PC World's Gadget Freak column and is author of Computer Privacy Annoyances (O'Reilly Media, 2005). PC World Senior Copy Editor Steven Gray, Richard Laermer of RLM PR, and freelance writer Phil Houtz also contributed to this story.