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 15 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

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?

Some hobbies take on a life of their own; others change the world. In early 1994, Stanford PhD 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 like 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.