9. "Room at the Top"
Petty was deep in the throes of depression after divorcing his first wife, Jane, when he sat down at a piano in the studio and poured his heart into this song. "I wish I could feel you, little one," he sang. "You're so far away. I want to reach out and touch your heart." The emotionally raw song kicks off Echo, a collection of tracks inspired by their breakup. "'Room at the Top' is the most depressing song I've ever written," said Petty, who hasn't played it a single time in the past 15 years. "I haven't even wanted to hear it. Though the last time I heard Echo, I did think, 'God, there's a lot more on here than I remembered.'"