First off, there’s Clippy, the awful Microsoft Office assistant. As James Fallows pointed out in his blog, “Clippy suffered the dreaded ‘optimization for first time use’ problem. That is, the very first time you were composing a letter with Word, you might possibly be grateful for advice about how to use various letter-formatting features. The next billion times you typed ‘Dear …’ and saw Clippy pop up, you wanted to scream.”
Next, there’s Comic Sans, easily the most misused font in the universe (I’m assuming if other planets have invented fonts they haven’t had one spiral out of control as badly as this one). It turns out that the face was designed for Microsoft Bob after Vincent Connare, the typographer responsible, saw an animated dog speaking in Times New Roman and thought it was all wrong (he spoke at ROFLthing yesterday).
On top of all this, guess who was a project manager for a short time on Microsoft Bob? None other than Melinda French, who now goes by the last name Gates and helps run a multi-billion dollar charitable fund. Fun facts abound!