For an artist who built his career on a certain degree of stubbornness, Wildflowers wasn’t just an admission of vulnerability; it was like standing naked in front of an audience. By the mid-1990s, after two decades of marriage, Petty was heading toward divorce—a personal cataclysm that would fuel much of 1999’s Echo. But you could hear the heartbreak coming on 1994’s Wildflowers, his second solo album, and one that features some of his most somber tunes: The title track finds him pining for a kind of beauty you can’t possess without ruining it, while the heartache in “To Find a Friend” is self-evident. “It’s good to be king/And have your own way,” Petty sings on “It’s Good to Be King.” Sure—but the subtext here is that it’s a kingdom of one. The magic, of course, is that despite the effort and attention that was put into the creation of Wildflowers, the album sounds natural and unforced—a sense of intuitiveness attributed, in part, to the influence of new producer Rick Rubin. Petty was writing from a quieter place now, and finding nuance in his solitude. And he was in a productive state of mind: Rubin said Petty once paused the tape between a demo playback and wrote an entirely new song, end to end, in a few minutes. The Rubin sessions would ultimately yield dozens of songs, and while Petty originally planned to make Wildflowers a double album, Warner Bros. didn’t think it warranted the length (a massive 2020 compilation, Wildflowers & All the Rest, would finally set those tracks free). But even in its original 15-track form, Wildflowers remains one of Petty’s greatest achievements—a surprisingly personal, deeply tuneful collection that finds Petty at his most vulnerable.