16. Apple Pro Mouse (2000)
In 1981, Xerox released the Star workstation, featuring a graphical interface and a two-button mouse. But Apple didn't get around to adding a second mouse button until August 2005, despite the fact that it had supported contextual menus in the Mac OS for years. This was especially infuriating when Apple released its sleek Pro Mouse in 2000: Instead of right-clicking to access contextual menus, Mac mousers had to hold down the Control key while clicking. Was this Apple's way of guaranteeing a steady stream of customers for multibutton mouse vendors like Logitech, Kensington, and Microsoft, or was it mere stubbornness? We're betting on the latter. In either case, it was annoying.
17. Plaxo (2002 to 2006)
Change the tiniest detail in your Plaxo contact profile, and everybody in your address book would receive a "Hi. I'm updating my address book. Please take a moment to update your latest contact information" email - a not-so-subtle nudge to get them to sign up for Plaxo themselves so that it would update such info without bugging anyone. Plaxo finally abandoned the practice in March 2006, saying it had accumulated enough members that spamming the world was no longer necessary. We had reached the same conclusion years earlier.
18. Microsoft Office Outlook 2003 (2003)
What do you call an email client that can't handle e-mail? Outlook 2003. Microsoft's premier email program stored all messages in a single, ever-growing data file. The more mail you got, the slower Outlook ran - until it stopped running entirely. Microsoft's solution? Autoarchive your messages, making them nearly impossible to find later or prompting annoying 'Would you like to archive your old messages now?' dialog boxes. No thanks, I'll just switch to Mozilla's free Thunderbird instead.
19. Apple Power Mac G4 Cube (2000)
Sure, the Borg-like design looked pretty darned cool. But the fanless 8in Cube was anything but cool in a literal sense. Put a pile of papers down on its top external vents, and the Cube would overheat and shut down. Worse, some Cubes shut down, hibernated, and restarted at random--over and over and over - due to loose DC-to-DC converter cards and finicky power buttons. That was most definitely uncool.
20. Harmonium (1998)
You've probably never heard of Harmonium, but you've certainly heard it at work - dozens of times a day. This software, developed by Finnish programmer Vesa-Matti "Vesku" Paananen in 1998 and distributed for free over the net, allows mobile phones to produce distinctive (one might also say cheesy) polyphonic ringtones. (Following them were master tones, which are snippets from actual songs.) The world has been a much noisier place ever since. Thanks for nothing, Vesku.