One simply has to marvel at a man who, in Microsoft, has built an unquestionable empire. However, nowhere in my years of following Bill Gates have I thought “I’d like to watch football and have a beer with that guy.” He has, in fact, always been portrayed as a man with no personality (if not an evil one). Think back to Pirates of Silicon Valley.

Tangent: I actually just had a conversation with a couple of co-workers last week about Geeks being the new Cool. It’s true. I remember somewhere around 6 or 7 years ago watching an episode of Buffy the Vampire Slayer (shameful, I don’t know why I just admitted that) where Buffy called a group of kids at her school “geeks.” These would be the computer lab-frequenting, Internet-savvy group of future business moguls she was referring to. I was insulted on behalf of all “geeks.”

Years later we live in a time where you’re not “with it” unless you have a Facebook account, the latest and greatest smart phone, and know who John Hodgman and Justin Long are. Even better, the more somebody knows about technology - the cooler they are.

Anyway … back to Bill. Jeff Hilimire forwarded me this video:

On the brink of departure from his day-to-day job at Microsoft (set for July), Bill decided to have some fun during a keynote at CES 2008 by showing a scripted, yet very entertaining video where we get a glimpse of how cool and fun he can actually be.

In a parody of what Bill’s last day on the job at Microsoft might be like, he endlessly pokes fun at himself - from workouts with Matthew McConnaughey where he’s told he’s “not ready” to take his shirt off, to an awkward experience with JayZee where his hopes of a rap career are dashed.

Sometimes the coolest people are those that embrace the parts of themselves that others might pick on. I had a blast watching this video!