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.

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.