Bill Gates, Super Model
This was fished out from some old teen mag spread (or something). We all have our share of embarrassing photos that we'd gladly burn but this, I believe, is in a league of its own. I ask you to especially take notice of the dreamy stare which must have turned millions of girls into infatuated fans back in the day. I thought that the .com boom was the first time the press actively portrayed tech as being cool and sexy but this proves that they had tried (and some would say failed) long before that.