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I admit this is a little weird. Someone commented in one of the feedback threads for Paris Hilton that he wondered if she would sign the cover to "One Night in Paris". In a thread for Jane Fonda someone had the same question regarding if she would sign the picture of her sitting behind the North Korean anti-aircraft gun. These got me wondering:

What picture would you like to have signed by someone that they probably wouldn't sign?

Personally, I'd like one of those cheesy Photoshopped topless pictures of Seven of Nine (from Voyager) or Princess Leah signed by the respective actress. Or some celebrity mug shots.

Axl Rose to sign anything already signed by Slash
Not sure if David Bowie would sign a Never Let Me Down album as he hates it so much that he even deleted one song from all re-releases

I think Bill Wyman on a Stones Photo