The temptation when trying to sum up a great musician’s legacy is to look beyond their most notable hits while still acknowledging that, yeah, those hits are really great songs. This is understandable; reducing any one artist’s canon to just a few “essential” works is a frustrating way to consider their entire career.
But boy, when we tried to make a list of 11 songs that explained Tom Petty, who died on October 2 at age 66, we found ourselves having to leave off so many big, well-known songs we loved. What about “You Don’t Know How It Feels”? Or “Runnin’ Down a Dream”? Or “Breakdown”? In this case, the hits were hits.
The fact of the matter is that Petty, as one of America’s finest musical chroniclers of itself, had too massive a career to encompass in just a handful of songs. The best way to understand him is to start with 1976’s Tom Petty and the Heartbreakers and move forward from there. But if you don’t have time to listen to 40-plus years of music, here are 11 songs to get you started.
“American Girl” (1976)
If Petty’s entire legacy were somehow reduced to just one song, it would probably be “American Girl,” the closing track (and second single) off Tom Petty and the Heartbreakers’ self-titled debut. With its nervously jangling guitar riff and its classic opening couplet (“She was an American girl / raised on promises”), the song declares its intentions almost immediately — something Petty was particularly skilled at.
But “American Girl” also gets at the heart of Petty’s great thematic concern: the lives of ordinary people who can’t escape either their circumstances or the perhaps foolhardy dreams they can’t give up. (Despite all of this, the song didn’t perform all that well on the US charts, never quite breaking into the top 100. It hit No. 40 in the UK.)
“American Girl” has come to stand for a certain kind of yearning Americana. It’s been used in TV and movies many, many times, recently closing out the Emmy-winning first season of The Handmaid’s Tale. No less than Hillary Clinton played “American Girl” at rallies in 2008, perhaps neglecting the ultimately prophetic line, “Ain’t it so painful / when something that is so close / is still so far out of reach.” Had this been the only song Petty ever recorded, it might be enough to cement his reputation. —Todd VanDerWerff
“Refugee” was the second single off Tom Petty and the Heartbreakers’ breakthrough third album, Damn the Torpedoes, hitting radio on the heels of the group’s first top 10 hit, “Don’t Do Me Like That” — which could easily be included on this list by virtue of that distinction. But “Refugee” is a better signifier of what made Tom Petty and the Heartbreakers so notable at the time, and what’s made both them and this song endure: the classic melodic rock ’n’ roll in its bones, down to its AABA structure, and the way it’s not beholden to the New Wave and punk stylings that defined much of American rock music at that time. Produced by pop mastermind Jimmy Iovine, the song might be the most rocking of Petty and the Heartbreakers’ enduring hits — and its music video, the group’s first, became a staple of early MTV, cementing the track’s legacy as a defining musical moment of the early 1980s. —Genevieve Koski
Petty’s collaborative generosity was one of his most defining characteristics as a musician, and there’s no better example of it than the song he co-wrote for Stevie Nicks. “Stop Draggin’ My Heart Around” was a hit single for Nicks’s first album, Bella, and the two went on to perform it together for decades. When Nicks opened for Petty’s 2017 40th-anniversary tour with the Heartbreakers, they leaned on this duet as recently as July to convey their deep, shared history as both towering musicians and fiercely committed friends. Petty called Nicks an “honorary Heartbreaker,” and together they broke millions of hearts into happy pieces. —Caroline Framke
“The Waiting” (1981)
Possibly based on something Janis Joplin said backstage at a concert, “The Waiting” gave us the immortal line “the waiting is the hardest part,” as well as the essence of what passes for optimism in Tom Petty’s world. Alongside dubious encouragement like “don’t let it kill you,” he promises he’ll be there to see the listener through the waiting — with a knowing subtext that the waiting never really ends. No wonder this song tied (with 1991’s “Learning to Fly”) for the title of the Heartbreakers’ longest-running No. 1 single on Billboard’s rock chart. —Aja Romano
In recent years, the 1985 track “Rebels” has mostly been discussed in terms of its place in Petty’s disavowal of his prior use of the Confederate flag, which he at one time displayed onstage while performing the song. Petty’s justification for what he calls the “downright stupid” decision to use the flag was that “Rebels” is about a flawed protagonist whom the flag represented, the so-called “Southern rebel,” a figure that permeates Petty and the Heartbreakers’ loose, ambitious concept album Southern Accents. The musical and cultural traditions of the American South have always percolated in the background of Petty’s music, but Southern Accents attempted to foreground them in a new, ambitious way that proved extremely taxing for both Petty and his band. In that respect, “Rebels” is also notorious for being the song that so frustrated Petty during its tortured recording process that he punched a studio wall and broke his hand. —GK
“Free Fallin’” (1989)
Also the soundtrack for a memorable Tom Cruise singalong in the 1997 Best Picture nominee Jerry Maguire, “Free Fallin’” became Petty’s biggest hit on Billboard’s Top 100 when it hit No. 7 in early 1990. It’s not just a great reminder of how good Petty was at capturing the gap between desire and fulfillment (explored through brief sketches of a number of figures in what amount to vignettes within the song itself) but also just how deep into his career he was when he released it. There are a few artists who’ve had their biggest hit 14 years after their first album (Aerosmith’s biggest chart hit, for instance, was the dreadful “Don’t Wanna Miss a Thing,” released in 1998, 25 years after the band’s debut), but few of those songs are as beloved or memorable as “Free Fallin’.” —TV
“I Won’t Back Down” (1989)
Written after an arsonist attempted to burn down Petty’s home in 1987, “I Won’t Back Down” is a response to a specific event that has become an iconic American song in large part for the malleability of that response. Petty’s signature straightforward, direct lyrics make “I Won’t Back Down” an all-purpose anthem of resilience and struggle against oppression, meaning it’s become a common soundtrack for political campaigns, sports programming, and protests of all stripes — and had a second life as a radio hit in the patriotic aftermath of 9/11.
That lyrical universality has contributed to the song’s status as both a cover-band standard and one of Petty’s most covered tunes — including, in a roundabout way, by one Sam Smith, who had to add Petty and co-writer Jeff Lynne to the credits for his massive hit “Stay With Me,” because its melodic similarities to “I Won’t Back Down” are undeniable (even if Smith claimed, somewhat outrageously given the song’s standing in the American rock canon, that he’d never heard the song before). —GK
“Into the Great Wide Open” (1991)
This classic Faustian tale centers on a young heartthrob musician who moves to the city with big dreams, only to get burned by the cold, heartless reality of Hollywood. The video stars Johnny Depp as the struggling rocker and Faye Dunaway as an industry femme fatale who lures him into a cameo-filled world of glamour and greed. On one level, the song fits into Petty’s thematic obsession with migration between rural and urban America and his anxiety over the corruption of the soul through exposure to city life. On another, more literal level, it describes Petty’s own hard-won battles against music studios for artistic control over his work. He appears in the video as a Wonka-esque master of ceremonies, coyly toying with the characters in his own personal circus; it’s a cynical nod to the industry’s deepening depersonalization and corporatization, a bird’s-eye view in which it seemed Petty peered uncannily into the future of the music business. —AR
“Mary Jane’s Last Dance” (1993)
Petty was middle-aged and at the peak of his career when he penned this anthem to small-town teenagers — which also doubles neatly as an anthem to weed. Petty was a self-described “reefer guy,” and his song about a girl (played by Kim Basinger in the famously creepy video) who singlehandedly causes the sexual awakening of all the boys in town will leave you both feeling hollow and wanting more. It’s a wry, self-aware take on the frustrations of feeling young and trapped, and the frustrations of addiction at any age. —AR
Against some of the other songs on this list, “Wildflowers” may seem slight in its simplicity. That space, however, is exactly where Petty thrived. This song, the title track off Petty’s second solo album, is in many ways the perfect distillation of how the rocker turned his love of Americana into something of a lullaby, a reassurance that you — yes, you — can take the time to soak up that patch of sunshine, that “you belong somewhere you feel free.” —CF
“Saving Grace” (2006)
Petty kept releasing new music, both with and without the Heartbreakers, well into the 21st century. His later work is more hit-or-miss than his earlier stuff, as you’d probably expect, but there are gems scattered throughout, particularly on the 2006 album Highway Companion, which captures both Petty’s restlessness and a new sense of mortality, which Petty ties to the endless roll of the road underneath a rocker’s tour bus wheels. (You can almost hear it in the chugging guitar.) This opening track neatly encapsulates Petty’s best late-period album. —TV
Correction: The original version of this article said “Learning to Fly” came out in 1981. It was released in 1991.