Hillwood highschool is the home the the hillwood hilltopers (more commonly know as the hillweed pill poppers). This school is full of ratchet ass hoes who would suck your dick for twenty bucks in the bathroom, and wanna be thugs who gamble in the bathroom and sell chips for a dollar.
Drinking at a completely inappropriate time or in an innappropriate place, such as during class, at a funeral, in the library, during a sports match (if you are playing) nine in the morning during finals week.
This term is a reference to the Denison UniversityHilltoppers, the men's acappella group (who are notorious for drinking in innapropriate occasions), but honestly a good percentage of the campus is equally guilty. Plus, we love them so, so it's okay. Sort of.
Someone that is commonly known as Hillary. Hillroy is the male counterpart for hillary. It also can be a nickname for somone named Hillary. And be used in the phrase: "Hillroy, my boy!"