Microsoft is nothing if not persistent. At times it's very Johnny-come-lately with its efforts, but you can never say it doesn't try. Kinda like Fat Joe. Take its search engine, for example. What started as MSN Search, part of destination portal, was succeeded by the underwhelming Live Search to compete with the ubiquitous search behemoth, and ruler of everything digital, Google. And now it has announced plans to replace that with an entirely new search platform called Bing.

Set to launch on June 3rd, Microsoft is hoping that Bing—which is supposed to bring to mind the sound of a bell ringing to indicate a search is done (we don't have a multi-million dollar R&D department, but wouldn't that be "ding"?)—will become synonymous with the verb "to search", the way "to google" is now. We won't rule anything out, but Microsoft has a hard road ahead of them. At least it's not the worst idea it's had. Take a look back at some of Microsoft's most famous misses...

• In an attempt to make Windows easier to use for the novice, Microsoft got the bright idea to create a $100 program called Bob which would replace the windows desktop with a more visual representation of a work space called the Public Family Room. Microsoft's current CEO was stated as saying that Bob was "one project we had undertaken ... where we decided that we have not succeeded and let's stop." 'Nuff said.

Why it failed: At $100 a pop, it was too expensive for most computer novices and if they really wanted a computer that was easy to use, they would just use a Mac. Not to mention, instead creating a patch for their poor user interface, Microsoft focused their efforts on Windows 95 which came with their new Explorer system which was way better than Bob.

• Normally, Windows gets a lot of shit for all their shortcomings, but no version of windows (or any other operating system, for that matter) has been the target of such vitriol as Windows ME. Released as a follow up to the Windows 98, ME was supposed to be the test bed for new Microsoft technology like System Restore.

Why It Failed: Nicknamed Windows "Mistake Edition", complaints of ME crashing users computers upon installation, it's inability to work with programs and hardware that worked fine on Windows 98 and the fact that some people couldn't even get the OS to shut it self down.

Microsoft Internet Explorer
• Even though the world's most ubiquitous web browser was lightweight, feature filled and pretty easy to use, like Windows ME, it became known as a symbol of Microsofts poor engineering.

Why It Failed: Being the most popular browser under the sun pretty much placed a bulls-eye on Internet Explorer, inciting every hacker to focus their cross-hairs on Microsoft's browser. It didn't help that Microsoft's security was worse than Hatton's guard. It was so bad, that in 2004 the U.S. Computer Emergency Readiness Team (CERT) told users to use any browser other than Internet Explorer unless they wanted to be infected with the Scob or Download.Ject keylogger that could be used to steal passwords and other personal info.

• Reportedly, one of Bill Gates favorite projects within in Microsoft was SPOT (Smart Personal Objects Technology). Included in this division was the MSN Smart Watch project which teamed Microsoft's MSN network up with watchmakers to create Dick Tracy type timepieces that let you check your email, the weather and headlines a glance at your wrist.

Why It Failed:To have all that data sent to a watch that looked like it came free with the purchase of Frosted Flakes, you had to fork over $40.00 a month.

• Microsoft's ill-fated music store sold files that were smothered in Windows Media DRM, but since they had no digital media player of their own, they created the PlayForSure standard. This let people know that no matter which MP3 player they bought (except for the iPod), as long as it had that certification it would play tracks from the MSN Music Store.

Why It Failed: Once Microsoft realized MSN Music couldn't compete with iTunes, they abandoned it and created their Zune brand. The problem? All the PlayForSure files could not play with the new Zune player. FAIL.