It was terrible marketing. Microsoft went through a period where they treated Apple as an ally instead of as the company that was eating their lunch, and it was reflected in their "just like Apple" advertising. Quirky music, aspiration lifestyle stuff -- that doesn't work when you're an underdog and someone else is owning the market. Microsoft seriously seemed to fear offending the Gruber and Sieglers of the world.

Their more recent advertising that goes directly at the iPad is much more compelling, and will have a very positive impact on their sales.