10) Paris Hilton might not be the best choice for an operating system that is famous for getting so many viruses, if you know what I mean. I'm not even sure if Microsoft can make a claim to simplicity if this is a reaction against Mac. But I guess you could try some random, photogenic K-5th grade kid using it in a school setting.
9) I agree with this nomination. Again though, I'm just not sure if it's a point Microsoft should be making. Especially with Vista.
8) I'd personally rather see Jimmy Buffet than Warren Buffet. It might not scream "Wall Street Success," but that's the point. It'll certainly distance Microsoft from the "business suit guy" image by appealing to a more celebrity style of success, built largely on the idea of relaxing at the beach.
7) I'm not even sure this is necessary, but if you wanted to play up the emotion card and you're dead set on using Oprah, you could have a sort of micro-interview of Bill Gates and focus on his Bill and Melinda Gates Foundation's charity work.
6) Well, the problem with looks is that Apple's visual appeal is also embodied in the computer it's running on, not just the OS. To be honest, I don't even think there's much very attractive about the Aero interface, so I'm having a hard time coming up with a stylish celebrity persona to match with it.
5) I'm pretty sure Al Gore wouldn't be up for it. Might go with Willie Nelson, again to distance the company from the "boring corporate" image and add that green cred.
4) No. Just... no. How about Richard Dean Anderson for versatility?
3) If we're going for characters instead of actual people, how about Robocop? Security, high-tech, crimefighting, superheroics, etc. The franchise also has that anti-corporate message, though in Microsoft's case that might backfire. Don't want folks to make the connection between MS and OCP. Also, the movies have a high gratuitous violence quotient, but then again so does the latest Bond movie.
Failing Murphy, how about R. Lee Ermey?
2) I have no problems with Jay.
1) I really don't know who could fill this role.