Listen to 14 Essential Tom Petty Songs

Tom Petty, who died Monday, was one of the quintessential American rock stars of the late 20th century. The remarkable streak of hit singles he wrote and recorded between 1976 and 1993 — mostly with his band, the Heartbreakers, but at times on his own or in collaboration with other artists — guaranteed that anyone who listened to the radio or turned on a television in those years knows at least a few of his songs by heart.

Petty’s music provided the soundtrack to countless parties and long highway drives; as much a pop hitmaker as a rock ‘n’ roll craftsman, he’ll be remembered for his instantly unforgettable choruses, and for how good it feels to sing along to them. But the accessibility of Petty’s work shouldn’t obscure the nuance that was often just below the surface. Here are 14 tracks that give a sense of the breadth of his catalog. Think of them as a can’t-miss playlist, and a prompt for further listening.

‘American Girl’ (1976)

It wasn’t a big hit at the time of its release, but this is the song that ensured Petty’s place in the American canon. The music is pure bar-band boogie, reflecting his journeyman years in Gainesville, Florida. And while “American Girl” sounds like sunshine, beer and smiles, a closer listen reveals it’s actually a song about disillusionment. (Note that the girl in the title was “raised on promises,” not on their fulfillment; by the second verse, she’s feeling desperate on a balcony.) Petty would continue exploring the subtle contradictions in America’s rock ‘n’ roll fantasy life for the next four decades.

‘Don’t Do Me Like That’ (1979)

Petty and the Heartbreakers’ first Top 10 hit is a masterpiece of efficiency — at 2 minutes and 44 seconds, it’s all hook. While histories of this era often emphasize the ways that punk firebrands reined in rock’s self-serious bloat, “Don’t Do Me Like That” is a reminder that Petty was doing much the same thing from well within the mainstream. In one of his most devilishly effective lead vocal performances, he made a needling sense of resentment sound like the most liberating thing in the world.

‘Refugee’ (1979)

The betrayal in Petty’s voice as he shouts the chorus is so piercing that it hardly matters whether anyone understands what, specifically, he means when he accuses his romantic partner of living “like a refugee.” The intensity of feeling is the point. At this stage in his career, he sang often about feeling ill-treated, but never with quite the electric charge heard here.

‘The Waiting’ (1981)

The 1979 album “Damn the Torpedoes" and its three hit singles made Petty and his band into major stars; by the time of its follow-up, “Hard Promises” (1981), he was a little more relaxed as a songwriter. That led to songs like this FM radio staple, where you can hear Petty’s love of the Byrds’ quite clearly, as he updates the older California group’s chiming chords and bittersweet yearning for a new generation. No longer needing to sell each song like it’s his only shot, he delivers the chorus with an understated smirk, like it’s no big deal — but good luck getting that melody out of your head after hearing it a few times.

‘Stop Draggin’ My Heart Around’ (1981)

If Petty had sung this one himself, as was the plan when he wrote it with the Heartbreakers’ lead guitarist, Mike Campbell, it would have been a very different song — maybe the second- or third-sharpest complaint issued by Petty on record in those years. The decision to let Stevie Nicks take it for her own solo album, prompted by their shared producer, Jimmy Iovine, was a stroke of genius: Her sublime sense of camp-tinged drama takes the song to a new level. Petty, who ended up singing just a few plaintive lines, is a perfect foil to Nicks, prompting generations of fans to wonder about an alternate reality where he, and not Lindsey Buckingham, joined her in Fleetwood Mac in the mid-1970s.

‘Rebels’ (1985)

Petty famously broke his hand in a fit of pique during the recording of the Heartbreakers’ 1985 album “Southern Accents.” That’s a high price for the music that resulted, but it was mostly worth it. “Rebels,” the ballad that opens the album, is uncharacteristically explicit about his ties to the American South — at times the lyrics read like his version of the Band’s “The Night They Drove Old Dixie Down” — but, true to form, any pride that’s there is undercut by darker notes of doubt and shame. It’s an unusual song, worth listening to if only for a fuller understanding of where he felt he came from.

‘End of the Line’ (1988)

On a break from the Heartbreakers, Petty ended up jamming in LA with his friends George Harrison, Bob Dylan, Jeff Lynne and Roy Orbison. Their 1988 debut as the Traveling Wilburys is mostly a curio for completists, but this gently swinging country tune is a gem that would have been a highlight among any of its participants’ solo releases that decade. The best part is the chorus, where a nonchalant Petty teases a former flame or friend: “Maybe somewhere down the road a ways / You’ll think of me, wonder where I am these days.”

‘Free Fallin'’ (1989)

“Full Moon Fever,” the solo album Petty released in 1989, is his second front-to-back classic LP (the first was “Damn the Torpedoes,” a decade before). Several of its songs, including the pleasantly defiant “I Won’t Back Down,” the delightfully bizarre “Runnin’ Down a Dream” and a spot-on cover of the Byrds’ “I’ll Feel a Whole Lot Better,” are among his strongest work. But the best and most important song on “Full Moon Fever” is “Free Fallin’,” the Top 10 hit that jump-started the second act of Petty’s career. It’s essentially an update on “American Girl,” veering between awe-struck longing for the narrator’s dream lover and biting sarcasm toward the same. But it’s a much kinder song: This time, he’s self-aware enough to acknowledge his own role in breaking her heart, and to admit he misses her. “Free Fallin'” marks the moment when Tom Petty proved he could handle the ‘90s.

‘Into the Great Wide Open’ (1991)

Lynne, who formed a close working relationship with Petty in the Traveling Wilburys and on “Full Moon Fever,” came along as a producer when the singer returned to the Heartbreakers fold in 1991. He’s the reason the group’s next album, “Into the Great Wide Open,” has that refreshed glow. The title track is an affectionate parable about a “rebel without a clue” named Eddie, who moves to LA and becomes a rock star. Everything seems to be going swimmingly, at least until the last verse, where our hero hears the words every major-label artist dreads: “Their A & R man said ‘I don’t hear a single.'” Petty makes you feel bad for the poor kid even as you laugh at his wry delivery.

‘Mary Jane’s Last Dance’ (1993)

Tastes change, but by this time it was clear that Tom Petty is forever. If “Free Fallin'” got Gen Xers listening to Petty, “Mary Jane’s Last Dance” was the THC-laced cherry on the intergenerational sundae. With its winking drug references, surreal humor and macabre music video — not to mention its instantly hummable chorus, given added punch by the producer Rick Rubin at the height of his powers — the song slid into Billboard’s Top 20, appeared frequently on MTV and handily reaffirmed Petty and the Heartbreakers’ place at rock’s forefront.

‘Wildflowers’ (1994)

Petty worked with Rubin again on “Wildflowers,” his next solo album. The hit from that LP was “You Don’t Know How It Feels,” a strong entry in the ongoing list of Tom Petty songs about feeling misunderstood and messed with. But the album peaks with its acoustic title track, one of his most tender and heartfelt love songs.

‘Walls (Circus)’ (1996)

Recording a full-length soundtrack for director Edward Burns’ romantic comedy “She’s the One” probably seemed like a great idea in the mid-90s, when Petty peers like Bruce Springsteen and Elton John were taking home Oscars for their own Hollywood work. The association with the film arguably just confused matters: The album the Heartbreakers made in 1996 is one of their strongest late-period releases, with no knowledge of the movie necessary to appreciate it. It’s fascinating to hear Petty and his bandmates adjusting to the eccentricities of the alternative-rock era, notably on their cover of an unprintably titled deep cut of Beck, as well as on this gorgeous psychedelic ballad. The chorus features some of Petty’s finest lyrics on the subject of romantic ambivalence: “You got a heart so big, it could crush this town / And I can’t hold out forever, even walls fall down.”

‘Free Girl Now’ (1999)

“Echo,” released in the period after Petty split from his first wife, is often short-handed as his divorce album, and while that’s a bit of an oversimplification, it’s a fascinating filter through which to view the album’s lead single. “Free Girl Now” is addressed to a woman who has just gotten out of a deeply flawed relationship: “I remember when you were his dog / I remember you under his thumb,” he notes. Now the woman is on her own, unbound, starting over. Petty sounds happy for her. (Is she the same woman from “American Girl” and “Free Fallin’,” whose titles this song cleverly riffs on? Maybe.) You get the sense that whatever the details of this possibly fictional breakup, and the role the narrator himself played in it, it means a lot to him that someone is living free.

‘American Dream Plan B’ (2014)

The music Petty made in the new millennium — including a 2006 solo album, three Heartbreakers LPs, and two more with his pre-fame band Mudcrutch — are all worth exploring for devoted fans, as are any number of bootlegs from Petty’s masterful live shows in these years. “Hypnotic Eye,” the final Heartbreakers album, is of particular note. On songs like this opener, he revisits the kind of hard-luck stories he wrote about through his entire career, with his balance of bitterness and hope more or less intact. “My success is anybody’s guess,” he grumbles here over a lowdown garage-rock crunch, “but like a fool, I’m bettin’ on happiness.”