Apple Fonts Are Target; Microsoft Fonts Are Walmart
Joel Spolsky has an interesting post on Safari for Windows, which highlights the different font philosophies used by Apple and Microsoft.
Apple generally believes that the goal of the algorithm should be to preserve the design of the typeface as much as possible, even at the cost of a little bit of blurriness. Microsoft generally believes that the shape of each letter should be hammered into pixel boundaries to prevent blur and improve readability, even at the cost of not being true to the typeface.
It is almost too easy to use this specific typography example as a larger metaphor for the Apple approach versus the Microsoft approach, in general.
Typically, Apple chose the stylish route, putting art above practicality, because Steve Jobs has taste, while Microsoft chose the comfortable route, the measurably pragmatic way of doing things that completely lacks in panache. To put it another way, if Apple was Target, Microsoft would be Wal-Mart.
Where does your brand fall on the practicality vs. style spectrum?