Clueless (1995)
Cher is a spoiled rich girl living in a mansion and attending school with a lot of other spoiled rich kids. But, unlike so many who have so much, she's not a mean girl. For example, when she sees the awkward new kid at school, her instinct is to extend the help she perceives is needed (makeover/boyfriend) rather than to shun her. Despite her desire to be a good person, her lack of knowledge of what goes on outside her bubble is a hindrance, so it's a good thing her stepbrother Josh is always around to keep her head from getting too big!
I really liked this when I first saw it 35 years ago (when I was still in my 20s). Though it doesn't entirely hold up, it's still pretty sweet and worth a watch.
C+