The 16 greatest moments in Web history

The Web has changed our lives, but what are the events that set its course? Here's our list of the top 16 defining moments

Depending on how you calculate it, the Web has been around for between 15 and 17 years -- which makes it old enough to ask for the car keys, but still an awkward teenager growing toward maturity. Yet it already has a long and storied history (and some prehistory). We've decided to chronicle its 16 greatest moments here.

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When possible, we pinpointed a specific day, hour, and even minute -- the "aha" moment when the people involved got the original idea, launched the site, sold the first product, or posted the first entry. Instead of listing the events chronologically, we've ranked them in ascending order of importance.

16. Scandal in a blue dress
Jan. 17, 1998; 11:32 pm PST: Drudge breaks the Lewinsky scandal.

"That woman": The Monica Lewinsky affair was an online scoop for The Drudge Report.

Love Matt Drudge, hate him, or think as little about him as possible, you have to give the muckraker (or is that pitchforker?) his due. One day after Newsweek killed a story about a new scandal in the Clinton White House, The Drudge Report broke the Monica Lewinsky story anyway. It was the first notable example of the Web scooping the national media, but it wouldn't be the last.

As when the telegraph supplanted the pony express, traditional media sources realized they could not compete with the immediacy of the Net and began scooping themselves, publishing stories first on the Web and later in print. Some publications killed their print editions to publish exclusively online; others redefined themselves or disappeared entirely. The Web news era had begun.

15. Do you Yahoo?
Feb. 1994: Jerry and David bookmark the Web.

Some hobbies take on a life of their own; others change the world. In early 1994, Stanford doctoral students Jerry Yang and David Filo posted a list of their favorite sites on the Web. The exact date they posted the links is lost to history, but we do know the list's original name: "Jerry and David's Guide to the World Wide Web." By April '94, it had a new tongue-in-cheek name: "Yet Another Hierarchical Officious Oracle," or Yahoo for short.

Yahoo represented the first attempt to catalog the Web, offering directory-style listings of every site that mattered -- with tiny sunglasses marking sites deemed truly cool. When providing exhaustive coverage became impossible, Yahoo was reborn as a Web portal, combining the directory with search, news headlines, instant messaging, e-mail, photo hosting, job listings, and assorted other services. As other major portals such as Lycos and Excite died off or were consumed by bigger fish, Yahoo continued to expand. Though surpassed by the Google search juggernaut, Yahoo may have memorable Web moments yet to come with cofounder Jerry Yang holding the reigns.

Blogs to wikis
In 2005, five bloggers did a heckuva job in real time tracking a natural disaster and its unnatural aftermath. A decade earlier, a Web site opened the world's largest ongoing garage sale. And at the turn of the millennium, a Web visionary began piecing together a compendium of all knowledge out of the clamor of thousands of contending keyboards.

14. Blogging Katrina
Aug. 28, 2005; 12:01 p.m. CST: The Survival of New Orleans Blog debuts.

As what was then a Category 5 hurricane bore down on New Orleans, Michael Barnes blogged: "We're on the 10th and 11th floor of a corporate high rise on Poydras Ave., right near St. Charles. We have generators and tons of food and water. It is 5 of us total. I am not sure how the Internet connection will be affected. I have a camera and my gun. .... Sustained winds are 175, gusts to 215. The real danger is not the wind, though, it's the storm surge the wind will be pushing into the city from the Gulf through the lake. The city might never recover. Honestly, this thing could be biblical."

Thus began what was for many the only eyewitness account of the worst natural disaster in our nation's history. For five days, Barnes and his coworkers rode out the storm and its aftermath, providing live reports and photos from their refuge in the downtown offices of Zipa Hosting and DirectNIC. Tens of thousands of Netizens visited the blog each day, getting a kind of personal coverage unavailable on CNN or inside The New York Times.

Barnes' moving account was proof that blogs could be more than just unsolicited opinions and self-obsessed ramblings -- they could serve as a valuable tool for recording and understanding the human experience.

13: Bidding for stardom
Sept. 3, 1995: eBay completes its first auction.

Not so long ago, the only way to get any return on the junk in your garage was to hold a yard sale. eBay changed all that. Now tens of thousands of small and medium-size businesses use eBay as their primary storefront, bringing e-commerce to the people.

According to eBay lore, the first item auctioned was a broken laser pointer that sold for $14.83, proving that someone somewhere will buy just about anything. Several billion dollars' worth of transactions later, the proof is on firmer ground than ever.

But eBay was also the first site to create a working reputation system on the Net, according to Chris Dellarocas, a business professor at the University of Maryland who studies how online reputations are formed. And as we move toward a world where your online reputation can make or break your ability to garner a job offer, get accepted into a school, or find a mate, this may ultimately prove to be a greater legacy.

"The fact that eBay was able to build a marketplace of 60 million people that works smoothly is a fundamental accomplishment," Dellarocas says. "They've built in enough trust so I can send money to a guy in Germany I've never met and expect to get what I've paid for in return. It's enabling us to have smoother transactions from any location -- to truly take advantage of the flat world the Internet provides."

12. Something Wiki this way comes
Jan. 15, 2001: Wikipedia posts its first entry.

Everybody's an expert. That phrase has never been truer than on Wikipedia, the online encyclopedia where anyone can add or edit entries on any topic, regardless of their personal expertise. Wikipedia now boasts 2 million articles in English (more than 7 million total) on everything from Aaargh! (a computer game) to ZZZap! (a TV show for kids).

Think of Wikipedia as an endless series of arguments, filled with edit wars and revisions to revisions, archived and identified by contributor. The result is a sprawling, anarchic, constantly changing resource that serves as many people's first stop when researching something on the Web (though, given the controversy over the accuracy of many entries, we hope it's not their last).

Creator Jimmy Wales doesn't remember the first Wikipedia entry, though he does remember the first words he typed into the wiki software: "Hello world."

"I think Wikipedia had a big impact on how people think about collaboration and knowledge, as well as the thinking about how to design security into social systems," says Wales. "We emphasized accountability and transparency over gate keeping. It was a philosophical change to leave things open, to make sure things can be fixed easily and you can see who did what, rather than pre-vetting contributors at the start."

A nation turned its lonely eyes to Jennifer Ringley and watched, stupefied. Oddpost made the experience of using a Web-based mail system feel as fast and efficient as working with a desktop app. Here are four more milestones in the development of the Web.

11. Candid camera
April 1996: JenniCam goes live.

For more than seven years, Jennifer Ringley trained the unblinking eye of a Webcam on her life -- first as a free art project, later charging subscriptions of $15 a year to cover bandwidth costs for the site's 20 million visitors. Though she occasionally appeared in the nude and had sex on camera, the content tended to be less pornography than a window on a tedious round of unexceptional experiences shared with everyone.

(Ironically, the once extremely public Ringley is now something of a recluse; e-mail messages we sent to her last known address went unreturned.)

But JenniCam paved the way both for a burgeoning X-rated cam industry and an entire generation of Web exhibitionists (see MySpace.com). It turned Orwell's notion of Big Brother on its ear: Instead of a government spying on us, we'd spy on each other (and maybe make a few bucks along the way). Reality TV shows such as "The Real World," "Survivor," and "Big Brother" and viral video sites such as YouTube owe a debt to Jennifer Ringley, who at least for a while made the mundane day-to-dayness of her life seem fascinating.

10. You and 3,255,620 of your closest friends
March 2003: Friendster makes the connections.

MySpace is huge and Facebook is the flavor of the month, but neither of them -- nor the gazillion other social networks that have sprouted up like kudzu -- would be here if it weren't for Friendster. Opening its digital doors to the public in March 2003, the site was the first to reveal the interconnections between its users.

Founder Jonathan Abrams says he came up with the idea for Friendster after being put off by the creepy anonymity of online dating sites. "I wanted a different kind of online experience that would integrate the online and offline worlds and bring your real-life social context with you onto the Web, something where you could network with people like we do in real life," he writes in an e-mail missive.

The idea caught fire. By July 2003, Friendster had more than 1 million users. But connecting the dots between that many people brought the site to a virtual standstill, and Friendster was soon surpassed by nimbler competitors. A series of bad business decisions didn't help. The story of Friendster became a textbook case of how not to manage a startup.

Ironically, Friendster is enjoying something of a comeback, riding the social networking wave that it helped create. In addition, Abrams has launched Socializr, a site that helps people plan social events in the real world instead of merely the virtual one.

9. Act globally, think locally
Oct. 24, 1995: Craig Newmark unveils his list.

Like many seminal Web events, Craigslist started out as a quirky side project seemingly devoid of commercial possibilities. In March 1995, Craig Newmark quit his job as a software architect for Charles Schwab in San Francisco and started a mailing list where subscribers could share information about interesting cultural events in the Bay Area.

"I was reflecting on how much people helped each other out on the Net, in those days, on the WELL and usenet news groups," he says via e-mail. As the list grew, people began posting messages looking for apartments, jobs, and other topics. In October of that year, Craig turned his private list into a public Web site at Cnewmark.com.

In September 1997, Craig's list became Craigslist.org. In early 1998, the site began charging a nominal fee for job listings (though the vast majority of ads remain free), and in 1999, Craigslist.org incorporated and began paying its employees.

Today, there are 450 local versions of Craigslist in 50 countries, and more than 25 million people visit them each month. The service has been credited (or blamed, depending on your point of view) with taking the classified ad market away from established newspapers. But Craigslist's greatest contribution may be in proving that, like politics, the greatest global movements are always local.

8. Odd pioneers
Feb. 16, 2003: Web mail service Oddpost debuts.

In 2003 anyone who used Hotmail or Yahoo Mail probably had a desktop e-mail program as well. That's because using Web mail services was torturous. Making any change to your inbox -- such as filing a message in a folder or deleting spam -- required lots of clicks and a round trip to the service's servers, while you drummed your fingers and waited.

Oddpost managed to make a Web mail service feel as if it were running on your hard drive. You could drag and drop message files to organize your inbox and preview messages instantly. Yahoo liked it so much that it bought the company and used the technology as the basis for its new mail service.

Oddpost powerfully illustrated what could be done within a browser, and soon that kind of functionality (based on programming platforms such as AJAX and Ruby on Rails) began showing up in Web-based word processors, spreadsheets, photo editors, and pretty much anything else a venture capitalist could shake a few million dollars at.

"127.0.0.1" doesn't sound as inviting as "home," and nothing draws a crowd faster than the promise of one-stop shopping. Our countdown continues.

7. URL be glad they did
June 23, 1983: The domain name system is born.

Thank Paul Mockapetris, Craig Partridge, and the late Jon Postel for the fact that you didn't have to type "70.42.185.10" to get here. Together they created the domain naming system, replacing numerical Internet addresses with English-language "domains" and introducing the nongeek world to joys of the backslash key.

Instead of having to memorize a 12-digit number for every host they wanted to visit, users could simply type the machine's name and domain. Servers set up across the network would then translate the words into numbers.

On that June day 24 years ago, a DNS packet first crossed the network and elicited a response, Mockapetris reports in an e-mail note. "That's my best estimate," he adds. "Nobody thought it was important, so no cameras were present or plaques made."

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