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Tom Petty’s 50 Greatest Songs

His hits have defined rock radio since the Seventies, and he never stopped writing great music. Here’s the definitive guide to his best songs

“It’s a strange to say out loud, but I always felt destined to do this,” Tom Petty told Rolling Stone‘s David Fricke in 2009. “From a very young age I felt this was going to happen to me.” From his early days as a hard-jangling realist amidst the fluff-addled Seventies, Tom Petty was always one of rock’s most enduring Everyman heroes, as well as one of the preeminent songwriters of his generation. A Tom Petty and the Heartbreakers show could reach the two-hour mark and not make it through all of his hits and memorable album cuts, or explore every nook of his career. And he was writing classic songs right up to the end. Here’s our definitive rundown of his 50 greatest.

44

“Peace in L.A.”

Days after the 1992 L.A. riots, Petty rushed into the studio with Mike Campbell to vent his frustrations and plead for calm. “I just had the feeling that the word ‘peace’ needs to be on the radio,” said Petty. “I quickly got on the phone, arranged the session, and then went into my little room and wrote the song.” It was on the radio just one day after they wrapped recording, with all profits from its release going to charities across L.A. “To this day I still get letters of thanks from missions in East L.A. because money keeps coming in,” he said. “I felt like we did some good.” 

43

“Yer So Bad”

The journey to making Full Moon Fever began by chance, when Petty and Jeff Lynne started talking while stopped next to each other at a red light on Thanksgiving 1987. Their first collaboration came soon after, with Lynne helping Petty figure out the structure of “Yer So Bad” – a song he had been struggling with. Recorded in Mike Campbell’s tiny-bedroom recording studio and garage, “Yer So Bad” is Petty at his most caustically hilarious: “My sister got lucky, married a yuppie/Took him for all he was worth,” he sings. “Black humor,” Petty said proudly. 

42

“Square One”

First heard on the soundtrack to Cameron Crowe’s 2005 film Elizabethtown, “Square One” received a proper release a year later on Petty’s criminally underrated solo LP Highway Companion. Co-produced by Jeff Lynne and Mike Campbell, the album exudes contentment and hard-won satisfaction. “It took a world of trouble, took a world of tears,” Petty sings gently. “It took a long time to get back here.” “I am pretty happy these days,” the 55-year-old singer said at the time. “I’ve gotten through the dark tunnel and come out the other side.” 

41

“Rebels”

“I wasn’t trying to cover the entire South and its story,” Petty said of Southern Accents. “I was trying to use it as a jumping-off place.” The narrator on the album’s towering opening track traces his own wild ways back to the South’s deep-seated rebel spirit. Petty wrote the song on a visit home to Florida and spent a year on it in the studio. The Southern Accents sessions were so difficult that at one point he punched a wall in frustration, injuring his hand. “I nearly blew it there,” Petty said later. “I almost didn’t play anymore.”

40

“Last Night”

The reggae-tinged “Last Night” is one of two songs on Vol. 1 where the youngest Traveling Wilbury sings lead vocals. The buoyant tune, which tells the story of a guy who has a one-night stand with a woman who robs him at knifepoint, ended up reaching the Top Five on the rock charts. But it wasn’t Petty’s first foray into reggae. He’d been a fan of the music since the Seventies, and he “tried to put some kind of reggae thing” into the second Mudcrutch single, “Depot Street,” from 1975. “I don’t think we were really successful,” he said later.

39

“Casa Dega”

This highlight of the six-CD Playback box set, with a groove that vaguely echoes the Zombies’ “Time of the Season,” was originally the B side of “Don’t Do Me Like That.” The song originated with a demo from Mike Campbell. Petty wrote the words on a plane after reading a New York Times article about a strange town in his home state. “There are all kinds of psychics and fortune tellers,” Petty said. “It’s this really small place. And I wrote that by putting myself in the mind of someone who went to Cassadaga. Though I spelled it wrong. … Poetic license, I guess.”

38

“Love Is a Long Road”

This churning rocker was co-written by Mike Campbell, who was inspired by a motorcycle he owned. “I was really into that frame of mind,” the guitarist said. “This feels like a motorcycle shifting gears.” Petty and Campbell recorded a demo that Petty described as “chaotic, with a lot of drum fills.” Jeff Lynne polished out the kinks with the help of a hard-hitting performance by L.A. session vet Jim Keltner, and the finished track rivaled “Runnin’ Down a Dream” in its sleek energy. “All of us had a hand in the arrangement,” Petty said. 

37

“Shadow of a Doubt (A Complex Kid)”

With a heraldic intro recalling the Who and an opening line that evokes the Drifters (“There goes my baby …”), this paean to a moody, mysterious girlfriend in open-A tuning came together quickly in the studio. Petty’s punk-Dylan lyrics were amusing – “And when she’s dreaming/Sometimes she sings in French/But in the morning/She don’t remember it” – but the emotion of “Shadow of a Doubt” rings true. As Petty sums it up, “It’s a good rock & roll song.” 

36

“Tweeter and the Monkey Man”

When the Traveling Wilburys released a song about two outlaws in New Jersey, crammed with references to Bruce Springsteen songs, some felt the supergroup was poking fun at the singer. “We weren’t trying to mock anybody,” said Petty. “Dylan said he wanted to set a song in New Jersey and use references to Springsteen songs. He meant it as praise.” Though one of Petty’s funniest songs, he didn’t play it live until his 2013 tour, which included his five-night stand at New York’s Beacon Theatre. 

35

“Dreamville”

Petty’s 2002 album, The Last DJ, was dismissed by some as a veteran rocker’s aimless primal scream against a changing music industry. (Many stations refused to play its anti-corporate title track, which Petty took as a compliment.) The album did have some fine moments, especially the gorgeous “Dreamville,” a nostalgic look back at his youth, when he bought guitar strings at Lillian’s Music Store and listened to early rock on the radio. “It’s one of the best songs I ever wrote,” said Petty. “That was about innocence, before the corruptions hit me.” 

34

“Two Gunslingers”

“A real good anti-war song,” Petty said of “Two Gunslingers.” Released months after the end of the first Gulf War, this Great Wide Open deep cut is a subtle demand for peace. Amid jangling acoustic guitars and cascading piano, Petty sings about two cowboys who are “takin’ control” of their lives and decide not to shoot it out, disappointing the assembled crowd that’s gathered to watch them battle. Petty said the germ of the song came from an old movie poster for the “terrible” 1967 Western Hostile Guns that a friend had given him as a joke. 

33

“Hometown Blues”

Written during Petty’s days in Mudcrutch, “Hometown Blues” was recorded with a unique lineup that included Florida musician Charlie Souza on sax, ex-Mudcrutch drummer Randall Marsh and Memphis soul legend Donald “Duck” Dunn on bass. “I could never get the right swing on it from Stan [Lynch] and Ron [Blair],” Petty said. “So I took that track and got Duck Dunn to play bass on it. He became a lifelong friend.” Petty engineered the track and his wife, Jane, helped out by lending hand claps.

32

“Lonesome Sundown”

The overwhelming bleakness of Petty’s most downcast album briefly lifts, at least for a verse or two, on “Lonesome Sundown,” and something resembling hope shines in. “Redemption comes to those who wait,” Petty sings over a slow, swaying country-tinged backing. “Forgiveness is the key/And I wish you love.” It’s a song about accepting loss and moving on, while also admitting that pain never truly goes away. “The words changed several times in that song,” said Petty. “I worked on that one a lot more than the others.” 

31

“American Dream Plan B”

“I knew I wanted to do a rock & roll record,” Petty told Rolling Stone of 2014’s Hypnotic Eye. “We hadn’t made a straight hard-rockin’ record, from beginning to end, in a long time.” The album recalled the tough, hungry intensity of the Heartbreakers’ debut and You’re Gonna Get It!, especially its gut-punch opening track, “American Dream Plan B.” The growling guitar riff is one of their hardest ever, and the lyric mixes resigned wit and up-against-the-wall defiance: “I’m half lit/I can’t dance for shit/But I see what I want/I go after it,” Petty sings. Amazingly, when Petty first played the song for his bandmates, they weren’t impressed. “Silence,” he said, recalling their initial response. “I said, ‘Listen, I think we have something here, but we’re going to have to get excited about it.'” Eventually, he brought them around, and it became one of their best late-period anthems, delivered with the fire of late-Seventies Heartbreakers and the feel and nuance of men who’ve been playing together for decades. “It’s that band 30 years later,” Petty said.