Wanna try to keep this thread going. I can't think of any shoots off the top of my head except for Alyssa Milano's Bikini Mag shoot.
Funny how Alyssa Milano was one of the real pioneers of the internet celeb craze. About 10-12 years ago there weren't many nude celebs on the internet (outside of Mr Skin) and Alyssa's early nude stuff started getting real popular. Alyssa and her mom would actually go on line and personally contact people and request them to remove them from forums and websites. Obviously they didn't want nude photos of Alyssa all over the place (shocking then, but routine now). I remember them saying something about they "didn't want her little brother seeing them".
Anyone remember that? Kind of sad actually, and it made you feel guilty looking at her, but it was a big deal back then. Now I think celebs just take it for granted if they ever do any nudity, it will be everywhere.
Alyssa's Bikini Mag pics would be a good addition. I heard she did them right after her 18th birthday, when she was literally "Barely Legal".