Can't Buy Me Love(1987)
To try and get out of his nerdy set, Ronald offers Cindy, cheerleader and school's most popular girl, a deal. She urgently needs $1,000 which he will let her have if she dates him for a month. Being desperate she grudgingly accepts, and soon starts to actually like him. But she finds his plan of becoming number one guy has worked and he has other fish to fry.
Originally posted to YouTube by dadsoldtapes, this is a TV spot for the movie.