Ricky Nelson - Poor Little Fool (1958)
This classic 50's song actually has a potentially happy ending. After a succession of bad romances, the "fool" finally finds true love, winning at "love's foolish game." The
final lines are deliberately ambiguous so as to give the young man his just deserts for playing other girls for fools in the past. But it is also a turning of the tables when the rake finally falls in love and ends up getting engaged, becoming a fool of a different sort. I had always missed this twist in the story.
"Poor Little Fool" was written by high school student Sharon Sheeley when she was only fifteen years old. She got Ricky Nelson's attention and convinced him to record the song ... which became the first #1 hit on the Billboard Hot 100 on August 4, 1958. It stayed at #1 for two weeks.