Tom Petty had just finished his 40th anniversary tour with the Heartbreakers when he passed away in October 2017, leaving behind a legacy of songs that blurred the boundaries between genre and generation. Influenced equally by his Southern roots and his West Coast migration, Petty’s music pitched its tent somewhere between rock ‘n’ roll, new wave, and Americana. It was a sound that nodded to past influences while staying firmly rooted in the present—and like the person who made it, it was utterly compelling.
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Here are five songs that define one of the most acclaimed careers in rock history.
5. “You Don’t Know How It Feels”
After years of successful collaborations with producer Jeff Lynne, Petty teamed up with Rick Rubin for his second solo album, Wildflowers. Most of the Heartbreakers played on the record, but Wildflowers sounded different than any Heartbreakers project before it, with a lean sound that often emphasized acoustic guitars over their electric counterparts.
Had it been released 20 years later, the album’s roots-rock singles would’ve dominated the Americana charts. Instead, Wildflowers arrived in 1994, a year whose No. 1 albums included Stone Temple Pilots’ Purple and Soundgarden’s Superunknown. This was the grunge era, which made songs like “You Don’t Know How It Feels”—a deliberate folk-rocker that moves forward at unhurried speed, punctuated by Petty’s harmonica—all the more unique for their sound and commercial success.
“Let’s roll another joint” wasn’t exactly an acceptable thing to sing during the Clinton era (even if you didn’t inhale), but that didn’t stop the song from becoming his 15th (and final) Top 40 hit on the Billboard Hot 100. “You Don’t Know How It Feels” marks another example of Petty doing things his way, ignoring the trends of a new decade and, instead, stripping back his sound to its rootsy basics.
4. “Don’t Come Around Here No More”
For many American rock bands who launched their careers in the 1970s, things got confusing during the following decade. Trends shifted, tastes changed, and MTV radically transformed the way people consumed music. Petty was one of the few frontmen to adapt to the new decade without uprooting the foundation of his sound.
Songs like “You Got Lucky” made room for the electronic textures of the era, too, but it was “Don’t Come Around Here No More”—the highlight of the Heartbreakers’ 1985 release, Southern Accents—that found Petty and company truly embracing the 1980s. Ambitious, psychedelic, and slathered with synthesizers, the song found Petty staking his claim in a digital decade. The trippy video was a hit, too, and featured co-producer Dave Stewart of Eurythmics dressing up in an Alice in Wonderland-inspired caterpillar costume, smoking a hookah, and playing the sitar.
3. “Free Fallin'”
Tom Petty had already logged a decade with the Heartbreakers by the time he began writing songs for his solo debut, Full Moon Fever, in 1987. Some of the Heartbreakers were openly dismissive of the new material. Drummer Stan Lynch refused to play on it, and bassist Howie Epstein walked out of the studio during the recording of “Free Fallin’.”
“I could tell that something was bothering him and I said, ‘Give us a minute, Howie, and we’ll be ready for you,” Petty explains in the Running Down a Dream documentary. “Then he said, ‘It’s not that; I don’t like this song.’ And I said, ‘Well, if you don’t like the song, then you don’t have to play it.’ And he said, ‘Right, bye.'”
Despite the absence of his bandmates (apart from Mike Campbell, whose guitar can be heard throughout), Petty soared high with “Free Fallin’,” whose No. 7 peak on the Billboard Hot 100 proved that even without the Heartbreakers, the guy could still break hearts. It wasn’t his first hit without the band, but it was certainly the biggest.
2. “I Won’t Back Down”
“I Won’t Back Down” isn’t just the title of Tom Petty’s fourth song to top Billboard‘s Mainstream Rock chart during the 1980s. It’s also a mission statement. Written one year after an arsonist burned his L.A. home to the ground in 1987, the song finds a defiant, resilient Petty standing up to all the opponents in his life.
[RELATED: What Do the Lyrics of Tom Petty’s Now-Politically-Charged Song “I Won’t Back Down” Mean?]
Petty already had a history of going toe-to-toe with bullies; he sued the B.F. Goodrich Company for mimicking his song “Mary’s New Car” in a TV commercial and, several years earlier, refused to let MCA Records jack up the price of his 1981 release, Hard Promises. “I Won’t Back Down” encapsulates that spirit. It’s driving and dogged, delivered by a singer who proudly called his own shots.
1. “American Girl”
Tom Petty and the Heartbreakers weren’t an overnight success in their homeland. Instead, the guys built their first following overseas, where “Anything That’s Rock ‘n’ Roll” became a Top 40 hit on the UK Singles chart in 1977. “American Girl” was released later that summer and also reached the Top 40.
Despite those British accolades, there’s something undeniably American about “American Girl,” and it’s not just the song’s title. After all, the song was recorded on July 4, 1976—not just the 4th of July, but the United States’ Bicentennial—and its melting pot of musical influences seems to mirror America’s own diversity.
With ringing guitar chords that saluted one of Petty’s longtime influences, The Byrds, “American Girl” bridged the gap between the jangling folk-rock of the 1960s and the punky spirit of new wave. It’s since become a staple of classic rock radio, too. It’s the rare kind of song that seems to belong everywhere, to everyone. That wide-ranging appeal is the genius of Petty, which is why “American Girl” tops this list.
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