Uptown Girl: Billy Joel & Christie Brinkley
Rumor has it that Billy Joel originally wrote "Uptown Girl" for then-girlfriend Elle Macpherson, but it stayed pretty relevant when he started dating another major supermodel, one Christie Brinkley. His soon-to-be wife starred in the 1983 video as, well, an uptown girl who catches the eye of an auto mechanic played by Billy. #TBT.