The Hot Chick (2002)

Decent watch, might watch again, but I don't think I can whole-heartedly recommend it.
This "body swap" trope is dealing with both sex swapping and age swapping, but not parent-child swapping, so a lot of things come with that in this silly dirt comedy. I'm not even sure you could make this movie in 2020, there would be too much heat from online communities. Just a "30 year old man" hanging around high schoolers, let alone young women, let alone young women that attract attention like these rich little brats do.
The writing is a lot of plot convenience, not only do they not immediately end up in jail, there are neglectful parents, school faculty, and far too many people to know about the situation and believe it. With the ratio of people that accept it, she could just live openly as a "girl in a mans body".
I do enjoy that the medium in this version is a pair of earrings, they make sense and keep you from thinking about it for too long.
Weirdly, they do manage to shift focus by writing in weird distractions all over the place, and it surprisingly helps with transitions: Adam Sandler a a fake rastafarian (I think at one point they agreed to always play racist roles in each others movies), a weird, but positive, racial identity plot, and even a dance club sequence that felt rather unecessary.
Now the point is that it's a comedy, and it should be funny, and it is, at times, but using potentially serious issues as comedy really distracts from the "I'm just having a good time" of it all, even when it's legitimately funny.
It's not that it's all bad, or that I don't like it, or like I won't watch it again, eventually, but there are a lot of movies to watch, and no one is missing anything from skipping this one.