P.S.: I will continue to post this message here, day after day after day, until somebody comes up with a guess. A person can only be ignored for so long.
Okay, Dan, I'm just gonna jump in and say it, and please don't take this the wrong way:
I have no idea who your mystery person is, and the reason I think we're all having trouble is because this person doesn't appear to have anything to do with "classic" movies. Jennifer Aniston, herself only 42 years old, has only been making films since 1988, so someone who was a child in one of her movies is unlikely to have appeared in a film that someone on *this* website would consider "classic" (not to be confused with a classically trained actor or an actor who has performed in a recent adaptation of a literary classic).
I'm sure these are all great clues you've given, and I'm intrigued to learn who this personage might be.......but there are some pretty film-savvy folks on this site (and I'm not referring to myself) and they would have gotten the answer by now if it was so "obvious".
So why don't you throw us another bone, containing any possible classic movie connection (if there is one), and we'll try to work it out.