“Rock and roll songs are just cheap shit—nothing deeper than that.” — Tom Petty

Tom Petty seemed to embody something that has always been perfect about rock ’n’ roll music. The spirit of the songs, at its purest, is one of freedom and unpretentiousness. It’s there in Chuck Berry’s odes to adolescent thrills, the nervous energy of Eddie Cochran, and the aching earnestness of Roy Orbison. And it’s there throughout the best songs from Tom Petty and The Heartbreakers.

Petty’s shocking death at age 66 stunned music fans because for the better part of 40-plus years, Tom Petty has felt like a musical institution. Unlike so many longstanding acts that approach such reverence, Petty’s music and persona carried a certain relatability. Whereas Bruce Springsteen brought working man-ism to near-operatic heights of drama and pathos, Petty seemed to wring truth out of simpler ambitions.

Petty’s early sound was most conveniently described as “new wave” to fit with the times but it didn’t have the urbane slant of English acts like Elvis Costello or Joe Jackson, and it lacked the obnoxious bite of East Coast-based bands like Blondie and The Cars. Tom Petty and The Heartbreakers specialized in a kind of rural New Wave that sounded more indebted to The Byrds than The Stooges.

Growing up in Gainesville, Florida, music was the young Petty’s refuge from a domineering, abusive father who despised Tom’s sensitivity and creative tendencies—but would later glom on to his son’s rock-star fame for status.

In the early 1970s, Tom formed his band, originally called The Epics, eventually changed to Mudcrutch, and finally, Tom Petty and The Heartbreakers (after Mudcrutch broke up following some failed 1975 singles). Even in forming The Heartbreakers, Petty was teaming with Mudcrutch holdovers Mike Campbell and Benmont Tench, alongside fellow Gainesville natives in drummer Stan Lynch and Ron Blair on bass.

Even through the end of Mudcrutch and formation of The Heartbreakers, there was a certain ethos that would form a foundation for the early days of Petty’s career and serve as guiding principles even decades later: a brotherhood with his bandmates in The Heartbreakers, and a defiant belief in the power of artistry and vision.

Producer Denny Cordell would famously sway the band after they’d agreed to sign with London Records, convincing them to sign with Cordell’s Shelter Records after they stopped in Tulsa at his offices on their way to the London signing in Los Angeles. “At the end of the day, he wasn’t going for the biggest deal he could possibly get,” Cordell said in the ’90s. “But he was going for the chance to make good records.” Shelter was co-founded by Tulsa native Leon Russell, and the label released Tom Petty and The Heartbreakers in 1975. The album flopped in America, but the band was a hit in the U.K.

Petty famously fought back against his label after Shelter Records’ distributor ABC Records was sold to MCA and he realized how much he was losing in a publishing deal he’d said he was forced to sign under duress. “My songs had been taken away from me before I even knew what publishing was,” Petty would later recall. And to free himself from the deal he filed for Chapter 11 bankruptcy, an unprecedented approach to battling his record company. Such a bold tactic meant that Petty wasn’t just fighting his label MCA; he was in a battle against the record business itself.

As he and Cordell’s relationship dissolved and The Heartbreakers’ second album, You’re Gonna Get It!, foundered, the battle raged in the media. The Heartbreakers embarked on “The Lawsuit Tour” and sold merchandise that included “Why MCA?” T-shirts.

“As soon as they thought my action might set an industry precedent,” Petty told Rolling Stone in 1980, “they rolled out the big guns. That’s when I realized these guys were mean. It was like they were after me just because I had the potential to do something. For that, they would destroy me—fuck up my brain to where I couldn’t do it anymore—before they’d let me do it for anyone else.”

Damn the Torpedoes (1979) would be Tom Petty and The Heartbreakers’ first platinum-selling album, but with status came another headache. Petty once again found himself at odds with the industry after realizing MCA was planning to sell his fourth album Hard Promises at a then-staggering $9.98, “Superstar Pricing” that was designed to make up for financial losses labels were enduring in the late 1970s. Petty fought against the price hike and won the hearts of fans, as Hard Promises would also be a platinum-seller.

Petty established himself as the sort of authentic rock artist whose ethics seemed almost antiquated at the dawn of the MTV era and amid the excesses of the 1980s. As punk, funk, and New Wave gave way to hair metal and dance pop, Tom Petty and The Heartbreakers stayed surprisingly fresh in changing times.

The video for their 1982 single “You Got Lucky” featured a Mad Max-inspired, apocalyptic storyline, evidence that the group wasn’t as resistant to the music video format as many of their peers. This would be more evident by 1985, with the release of the popular Alice in Wonderland-themed visual for “Don’t Come Around Here No More”—a synth-driven hit by Petty and co-written and co-produced with Dave Stewart of Eurythmics.

“Don’t Come Around Here No More” was a major hit from the Heartbreakers’ 1985 Southern Accents album, but the LP was a source of tension within the band. Accents had originally been conceived as a concept record about Southern culture, but the inclusion of Stewart muddied the theme. Nonetheless, on the Southern Accents Tour, Petty included merchandise and stage dressing that prominently featured the Confederate flag. It was a move he would come to regret.

“ The Confederate flag was the wallpaper of the South when I was a kid growing up in Gainesville, Florida,” Petty would say in 2015. “I always knew it had to do with the Civil War, but the South had adopted it as its logo. I was pretty ignorant of what it actually meant. It was on a flagpole in front of the courthouse and I often saw it in Western movies. I just honestly didn’t give it much thought, though I should have.”

“In 1985, I released an album called Southern Accents. It began as a concept record about the South, but the concept part slipped away probably 70 percent or so into the album. I just let it go, but the Confederate flag became part of the marketing for the tour. I wish I had given it more thought. It was a downright stupid thing to do.”

A sticking point for Petty was when fans began to bring Confederate flags to shows. In 2010, Fred Mills of BLURT recalled seeing Petty live in 1990 (with Lenny Kravitz opening, no less) when a fan tossed a Confederate flag onstage.

“A certain yahoo element had already been making its presence in the crowd known, emitting whoops and raising beer cups whenever Petty would make a regional reference. It was starting to feel like a NASCAR rally in the arena. Now, as the band eased into the song’s signature piano intro, somebody tossed a folded-up object onto the stage,” said Mills. “Petty walked over, picked it up, and started unfolding it: a rebel flag, symbol of the Confederacy—and of a whole lot more. He froze, uncertain as to what he should do. Well, wave it proudly at all your fellow Southerners, you could almost hear the collective thought ripple through the air. Instead, Petty walked back to the mic, still holding the flag, and slowly began to speak, talking about how on the Southern Accents Tour a few years ago they’d included a Confederate flag as part of the stage set, but since then he’d been thinking about it and decided that it had been a mistake because he understood maybe it wasn’t just a rebel image to some folks. As a low rumble of boos and a few catcalls came out of the crowd, Petty carefully wadded the flag up and concluded, ‘So we don’t do’—nodding at the flag—‘this anymore.’ Glaring at it one last time and then chucking it back down, he glanced at the band then launched directly into the next song.”

Petty’s success in the late 1980s with the multiplatinum Full Moon Fever (his first official solo album) and the Traveling Wilburys made him one of the more venerated “elders” of the MTV generation, and it also emphasized Petty as a conduit that connected three musical generations of rock. Even as pop culture became dominated by grunge and gangsta rap in the 1990s, there was Tom Petty, consistently charting with hit singles like “Into the Great Wide Open” and “Mary Jane’s Last Dance.” And he and The Heartbreakers had toured with Bob Dylan, played with Johnny Cash, and written hits with George Harrison and Roy Orbison. Even his most famous producers—Jimmy Iovine, Jeff Lynne, and Rick Rubin—represented entirely different generations and approaches to rock music.

In the 2000s, Petty continued to rankle the suits—albeit more as a cantankerous elder statesman than brash upstart—most notably on 2002’s The Last DJ, which railed against commercial radio and the hollowness of the modern music industry. And he and The Heartbreakers continued as one of rock’s most successful institutions. Along the way, there had been scars (the 1994 firing of Stan Lynch, Petty’s 1996 divorce from his first wife Jane, and Howie Epstein’s death in 2003 from a heroin overdose) but Tom Petty seemed to be a permanent fixture in the musical firmament, forever playing a gig and reminding fans everywhere just how many of his songs had been a part of their lives.

Tom Petty’s journey came to an unexpected end on Oct. 2, and it may be hard for some to recognize why this old rocker meant so much to so many people across so many generations. Tom Petty was possessed of the kind of easygoing coolness that you took for granted until it was staring you in the face, his songs sounded simple but burst with ideas and subtext, and his band was fucking sick without ever seeming showy. He was ballsy enough to do things his way and honest enough to admit when his way had been flat-out wrong. We’ll always have the songs. But man… we are really going to miss having him.