The world's coolest Chief Counsel?
I think you can make a serious case for Sun's Mike Dillon as the world's coolest Chief Counsel. Where else will you find an executive who dresses up as a pirate, is obsessed with the Tour de France, goes to Maker Faire, rides a vintage motorcycle, and goes sea kayaking in the arctic for vacation? Not to mention intentionally simplifying legal documents, challenging patents, and questioning the actions of the RIAA. If you're not yet reading his blog, click on one of the links and start reading - it's all worth your time.
I've had a couple of occasions to interact with Mike over the last couple of years and I'll award some bonus points for his being a really nice guy.
Almost makes me reconsider law school.