I went to high school with Cris Judd (ex Mr. Jennifer Lopez); we were in the same graduating class (Niceville, FL Class of '87). I remember him as being in a class or two of mine, but he was neither a band nor drama geek so I didn't actually know him well. I also went to school with filmmaker Carlos Larkin, but nobody's ever heard of poor Carlos.
When I worked at Universal Orlando, I met Jodie Foster and Barbara Eden and Cedella Marley. I worked there when they were first trying to make Jodie Foster's pet circus-movie project Flora Plum, so Russell Crowe was at one of the soundstages for a while. One of my bosses was scheming to get me a blind date with him, but I dorked out about eating a hot dog once within his field of vision. So, alas, I was never actually introduced; I was too deliciously mortified to let Richard drag me out there anymore. Sigh. I'm sure Russell still thinks back on the ubergeeky woman pointed out to him once in Florida and fantasizes about "what might have been....."
(Hey, don't burst my bubble on this one.)
Also met MaryAnn Mobley, Gary Collins, Doug Hutchison, and I used to take dance classes with a girl named Tammy Ammerson who went on to a role on One Life to Live as a teenager in the late 80s. No idea where she is now.
ETA: Oh, and Anne McCaffrey is a super-beeyotch who hated my anonymous guts for "causing trouble" in her fandom and later on her website. Really, that woman is a piece of work.... <grimace>