Well, confession time: when I was 14 I went through a Madonna phase.
Wipe that smirk off your face! Don't tell me that you didn't have one, too.
I really liked her stuff and listened to it all the time. My introduction to her work came at the age of thirteen with this video of Like a Prayer
A few days ago, my wife and I heard the playfully romantic pop song True Blue, which is among our favorites:
My favorite Madonna song is the obscure but joyful celebration of childhood Dear Jessie. I especially like its use of stringed instruments: