4. Say Anything
Date: 1989
Starring: John Cusack, Ione Skye, John Mahoney
Reason to watch it: John Cusack saying, "I don't want to sell anything, buy anything or process anything as a career. I don't want to sell anything bought or processed ... or buy anything sold or processed ... or process anything sold, bought or processed ... or repair anything sold, bought or processed. You know, as a career, I don't want to do that."
Lloyd Dobler (Cusack), quintessential man at the age of 19, flustered young'un in love with Diane (Skye), blends the perfect combo of eccentricity, love and forlornness, and he does it in such a way that you won't feel ashamed for watching a movie about a fumbling high school boy crushing for a gorgeous girl. What makes it even more difficult is Diane's father (Mahoney), who lives vicariously through his daughter's academic aspirations and is anti-Lloyd with no shame. Teen angst at its best. And John is just so damn lovable!
5. Purple Rain
Date: 1984
Starring: Prince, Apollonia
Reason to watch it: For goodness sake -- it's Prince back when he was a real man with a real name!





