Meatballs III: Summer Job (1987)

Getting into heaven is tough, just ask dead porn star Roxy Doujur.  To earn her wings, she is sent back to earth to help hapless, nerdy virgin Rudy (Patrick Dempsey) unburden himself of his eternal-cherry. Rudy is working at a river resort and has the hots for the wife of “Mean Gene” his tyrannical boss.  Will there be enough divine intervention to help Rudy get to the Promised Land?

Before he was “McDreamy”, Dempsey was a 21 year old looking for his big break.  Ours comes in a brief scene that unveils a clear shot of his young, slim rear end.  Knowing what he’ll develop into, this is like looking into a crystal butt and knowing the fabulous future.