Back when I taught Windows apps for a living, I began each class with some kind of mood-setting icebreaker. For instance, those of you with a tech background may be surprised to learn that it will never occur to the average PC user to clean their mouse. I showed ’em how: I popped the ball out of the mouse and gave it a quick puff to blow the dust out.

From the reaction, you might have thought I’d done it to a real mouse.

I’m thinking, now, that it must have occurred to many of my students that there’s a crude yet logical name for this procedure, a name that it would have cost me my job to actually say.

But when it was a MS Office application, I had a ready-made icebreaker built into the software. A feature that the whole suite shares. A feature that everyone has used, since it pops onto the screen unbidden. A feature that users hate with a passion I’d previously seen reserved for the post office, the phone company or used car dealers.

Yes, I’m talking about Clippy, the paperclip, the Office Assistant.

I told his story in a roundabout way, because (as just now) I didn’t tell the class the point of what appeared to be a digression. I talked briefly about the forgotten Microsoft product, in which Clippy (and several of the other Office Assistant characters) had made his debut. A product intended, as Clippy is now, to put a friendly, happy face on the user interface, to help users overcome their fear of the PC (yes, average users are afraid of their computers), to reassure them that the computer is there to do what they tell it to do, no less, no more.

The lesson learned from this product is, as frustrated as you may get with your computer and the software it runs, Microsoft is at least trying to help. Only a deeply-felt concern for the lost user could have persuaded them to let this thing out of the gate. Shed a tear for broken dreams.

I give you’s Worst Computer Product of the Decade: Microsoft Bob.

(See also Wikipedia and ToastyTech.)