16. Apple Newton. It's no iPhone, but by some measures the Newton still beats the pants off any PDA since. Rabid fans wax nostalgic about the Newton OS, and breathy rumors of a new Apple PDA remain a staple of Macworld Expos. Alas, the Newton never had a chance. Introduced in 1993, the Newton MessagePads were bulky, with lousy battery life. While Palm and Microsoft's PDA partners were building devices that could actually fit in your pocket, Apple answered with a full-sized keyboard and a clunky clamshell for the Newton eMate 300 in 1997, then threw in the towel as its losses mounted.

It's a shame. With some software tweaks to suit business users, the iPhone and the iPod Touch could get Apple back in the game. But given the bad taste left by Newton, who'd be brave enough to suggest it to Steve now? (Besides us.)

15. Palm OS Cobalt. The only thing worse than giving up on a viable market is to win it totally, then run it into the ground. What else can be said about Palm? Its devices were revolutionary, its competition from Microsoft laughable. Then came years of mergers, acquisitions, spin-offs, and rebranding. All the while, the products stagnated. When Palm finally delivered its Cobalt OS in 2004, the purported successor to the aging Palm OS failed to win any licensees.

Now, Palm is resorting to a Hail Mary: The next Palm OS, we're told, will be based on Linux. But when it might appear is anyone's guess, and by then it won't matter. We'll all be too used to this year's Treos, running Windows Mobile.

14. Netscape 6. The turning point of the browser wars came in 1997, with the release of Internet Explorer 4. For the first time, IE was better than Netscape Communicator. Not only was it faster, but it had more features and better standards compliance.

Netscape should have struck back immediately, but instead it dragged its feet. As Microsoft pressed ahead with IE5, Netscape's open source Mozilla project foundered, producing nothing but buggy "preview releases." When Netscape 6 finally appeared, years later, it was a bloated, sluggish mess. The war was lost, and now even the Netscape brand is scheduled to pass into oblivion.

Ironically, the former Netscape Communicator suite lives on as an open source project, called SeaMonkey -- presumably because it sounded great at first, but the real thing is a disappointment.

13. Search portals. Where are they now? At the height of the dot-com boom, Web surfers had a plethora of search engines to choose from: AltaVista, Excite, InfoSeek, Lycos, and many more. Today, the major players of the past are mostly dead. A few have soldiered on, such as Ask.com, but only after repeated redesigns.

Chalk it up to old-fashioned hubris. Instead of concentrating on their search offerings, the first-generation search engines fell victim to the portal arms race. They built up dashboards full of sports scores, stock quotes, news headlines, horoscopes, the weather, email, instant messaging, games, and sponsored content -- until finding what you wanted was like playing Where's Waldo. Neither fish nor fowl, they became awkward combinations of search portals and general-interest portals. The world went to Yahoo for the latter. And when an upstart called Google appeared with a clean UI and high-quality search, users told the other engines to get lost.

12. IPv6. Few topics spark more debate than IT's equivalent of global warming. According to some experts, the question isn't whether we will run out of IPv4 network addresses, but how soon. And there's no Kyoto controversy here; federal policy already requires that government offices transition to IPv6 by 2008. So why is everyone still dragging their feet?