Even through her often catchy and provocative songs and videos, Madonna has had some pretty heartbreaking songs/moments.
- "Bad Girl" from her Erotica album tells the tale of a Broken Bird who tries to dull the pain of her life through smoking, drinking and casual sex. The music video ramps it up by having the latter vice cause her death, having been killed by one of the men she regularly took home.
- "This Used to Be My Playground" from A League of Their Own, itself with plenty of tearjerking moments. The lyrics don't spare what she's feeling, either:"Wishing you were here with me..."
- Tellingly, neither song has ever been played in concert since their releases.
- "I'll Remember" from With Honors is a beautiful send-off to losing anyone in your life, be it through distance or death.
- "Papa Don't Preach" from her True Blue album, which has the song's subject matter practically begging her father for his approval after getting pregnant out of wedlock.
- Similarly, there's "Live to Tell" from the same album, which showcases someone going through periods of self-reflection and self-doubt:"If I ran away, I wouldn't have the strength to go very far..."
- Doubling as awesome, her tribute to Michael Jackson at the 2009 MTV Video Music Awards. One particularly poignant line from when she addressed the audience expresses disappointment and dismay at how much people had abandoned Michael in his final years, herself included.
