In 1987, he participated in Meatballs 3, where he played a janitor, Rudy. This movie gave him some fame. Soon after, he married actress Rocky Parker, twenty seven years his senior.
It wasn't until another 1987 release, ''Can't Buy Me Love, that he achieved major movie star status. The movie, in which he played Ronald Miller, was a geek to popular type of comedy which launched him and co-star Amanda Peterson to teen idol status, and Dempsey and Peterson appeared constantly on the covers of such teen magazines asTeen Beat, Tiger Beat, [[16 {magazine}|16]], Bop and others. In 1989, he shared credits with Charo and Kristy Alley in Loverboy'', where he played a pizza delivery boy.
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