Top 10 worst Microsoft products of all time

2. Clippy
Shaun Nichols: Bob was regarded as one of the more amusing failures in Microsoft's history. An early attempt to simplify computer use, Bob was instead received as an annoying gimmick that drove people crazy.

You would think that after such a fiasco Microsoft would learn its lesson, but no. With the bitter taste of Bob still lingering, Microsoft set out to create an even more useless, intrusive and irritating piece of idiotware: Clippy. The infamous animated paper-clip shipped with Microsoft Office 97-2003 had a six-year run which tortured users and gave office supplies everywhere a bad name.

Think of the annoying salesperson who pops up behind you and repeatedly asks if you're finding everything OK, or the guy who stands over your shoulder while you're fixing something in the garage and offers unwanted advice. Clippy was like both of those people, combined with an irritating children's cartoon character. Obviously, when you're on a deadline and rushing to finish a business report or term paper, nothing is more helpful than an annoying cartoon paper clip popping up on the screen and offering to help you write up your grocery list.

Thankfully Clippy was killed off in the most recent versions of Office. Hopefully Microsoft has finally learned its lesson and we won't have to deal with an even more annoying animated utility in the future, but I'm not optimistic.

Iain Thomson: Microsoft has never released the name of the person who came up the idea for Clippy, and for good reason. Several million computer users would be after them with murder in their hearts and police wouldn't have to look far for a motive.

I swear IT administrators got more calls about Clippy that any other piece of Microsoft kit. The overwhelming question was how to turn it off before people snapped and took a chainsaw to their PCs. It was a nadir in stupid software.

You have to wonder what Microsoft was thinking. Maybe there were some science fiction fans at the company who liked the idea of a computer helper. But Clippy wasn't a HAL or other advanced AI system. It was AD – artificial dumbness. It's still a running joke in the industry and I hope it remains so; that way no company will be so stupid as to do it again.

1. Windows Me
Iain Thomson: When we decided to do this list I was dreading the argument with Shaun. I know he hates Vista and would want it for the top spot, but I felt we'd be not just flogging a dead horse but jumping up and down on the tins of dog food it had become.

As it turns out, he wasn't keen to have Vista on the top spot either and we quickly agreed on the winner, if that's the word. Windows Millennium Edition (Me) was an absolute dog of an operating system and even now is mocked as Microsoft's lowest point in operating system design.

To start off with the operating system was, in my opinion, the most crash-prone piece of software I've ever had the misfortune to run. It was as unstable as a Hollywood starlet with substance abuse issues, and many users got used to saving everything every five minutes just in case. IT administrators hated it for this reason and point-blank refused to roll it out in more than a few instances.

Then there were the compatibility issues. To speed up the boot time Microsoft limited access to DOS, but this also made some popular applications incompatible with the operating system. The system restore feature was a nice idea, but most users assumed that documents would also be restored, which wasn't the case, and occasionally even found the system restored deleted malware.

There was a widespread view that Me was a cash-in product, something Microsoft had stuck out there early to wring a bit more cash out of the Windows 9x line before moving over to XP. That may or may not be true, but it was certainly not a polished product and did wonders for sales of Apple's iMac.

Shaun Nichols: When users restored their systems with Windows 98, the software would occasionally also reinstall malware which had previously been deleted. Amazingly, the fact that it would deliberately reinfect your computer was not the worst thing people remember about Windows Me. That should tell you all you need to know right there.

Windows Me was one of those releases that Microsoft really should never have let off campus. After the first few tests, which no doubt showed that the system was incredibly error-prone, someone in the higher ranks of the company should have pressed the panic button and sent everyone back to the drawing board. It's hard to imagine a Steve Jobs or a Larry Ellison letting a dog of this calibre ship as a final release.

Last week Iain suggested that every other version of DOS was poorly built and worth skipping. I would suggest that the same holds true for Windows: 3.11 was a landmark release, Windows 95 not so great, Windows 98 much better, Windows Me was notably terrible, Windows XP very good, and Vista a train wreck. The good news is that, if history is any indication, Windows 7 shouldn't be so bad.