I think somebody should study how MS marketing works, make it a case-study. Every time they try to be "hip", they end up looking like fools. Remember that weird Seinfeld ad? The spooky over-polished family for Windows 7? The competition on "speed-of-opening-apps" on WP7 where nobody was allowed to win? When they stick to the basics, they usually manage to be half-decent, like for the Windows 8 campaign: safe, complet…
All in all, the Windows 8 ads are IMO fresh, and definitely leaning more towards the younger adult hip side. And they're pulling it off pretty nicely.