Tech's all-time top 25 flops: No. 16 to 20
20. Copland. Some fumbles can be recovered. And it's true; today, Mac OS X is an impressive operating system. But imagine how much further Apple could have gone if it had delivered its next-gen OS when it originally intended to, back in 1995.

Copland was meant to be the modern successor to the original Mac OS, but years of political infighting had hobbled Apple's development department. For all its superior engineering talent, it became clear that it was impossible for Apple to produce a modernized Mac OS on its own. Instead, it would buy Steve Jobs' NeXT OS and use that as the basis for the Mac OS X that ultimately shipped in 1999 -- ironic, considering that Jobs had left Apple over political infighting a decade earlier.

19. Gnu Hurd. When Richard Stallman launched the Gnu project in 1983, his goal was to build the world's first completely free operating system: kernel, tools, utilities, applications, documentation, and all. Good thing he didn't start from the bottom up.

Almost 25 years later, there is still no Gnu kernel. The Hurd, as the proposed kernel is known, should have been the Free Software movement's crowning achievement. Instead it's become the poster child for collaborative software development gone wrong, topping the lists of vaporware year after year. And it's a shame -- because wouldn't it be great if there was a free OS kernel for everyone to use?

18. Oracle Raw Iron. What's the best OS for your database server? Should you run it on Windows? Linux? AIX? Something else? Back in 1998, Oracle's answer was none of the above! Instead, Larry Ellison promised an "appliance" version of Oracle 8i, called Raw Iron, that ran atop the bare server hardware. No longer would Oracle customers need to worry about a separate support contract with an OS vendor: Oracle would handle the whole show.

Behind the scenes, prototype Raw Iron boxes ran a custom version of Sun Solaris, but it didn't matter. Customers had seen through Larry's hand-waving, anyway. When nobody bit, the project was quietly shelved -- just a few years before the market for network appliances took off.

17. B-to-b e-commerce. As the dot-com craze waned in the early 2000s, venture capitalists clung to a last-ditch idea: If all those startup e-commerce companies weren't striking gold with the consumer public, maybe they could ply their wares to other, more established companies instead? They called it b-to-b e-commerce, and a generation of would-be digital disintermediators was born.

The problem was that few of their potential customers were interested in cutting out the middlemen -- not if it meant trading them for an unproven online startup with a tiny sales force and no real experience in inventory management. In the end, though, the b-to-b players did deliver some excellent deals -- when their assets were offered up at auction.

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.)

Top tech flops Nos. 21-25: PS/2, VR, compression wars, ...
Top tech flops Nos. 16-20: Copland, Gnu Hurd, Oracle Raw Iron, ...
Top tech flops Nos. 11-15: Palm OS Cobalt, Netscape 6, search engines, ...
Top tech flops Nos. 6-10: Itanium, Mac clones, e-currency, ...
Top tech flops Nos. 1-5: DRM, paperless office, iPod imitators, ...