In 1979, I was an undersized FM-generation high-school junior with a voice that wouldn’t change, a stressed single mom, and a bedroom in a rented gray two-family house in which I had to play my stereo low so I wouldn’t disturb all the people living close around me. And then my daily affront at this complete lack of agency found validation when some skinny blond dude calling his album “Damn the Torpedoes” uplifted my evenings with a simple phrase about being cut down to size on a regular basis: “Don’t do me like that.” He wasn’t celebrating humiliation—he understood the condition, which is, foremost, the inability to make the humiliation stop. There was nothing to do except to say to hell with annoying Mom and the neighbors and, in my alarmingly pitched treble that sounded like a radio veering between frequencies, to sing out that ambrosial phrase right along with Petty: “Don’t do me like that.”

Tom Petty and the Heartbreakers have been filling the air with pop masterpieces for forty years now. Their hits have spent so much time in cars, in grocery aisles, in offices, and on beaches, and have such aural clarity that they are instantly individuating—you can be immersed in your own business, busy with tasks, and within three bright chords you are sure to recognize “American Girl” or “Runnin’ Down a Dream” or “I Won’t Back Down.” That kind of cultural endurance is sufficiently unusual that this summer, during what Petty has said is the band’s final big tour, I have found myself circling back and wondering what it is about Petty that’s kept him so much around. Certainly, Petty’s early embattled lyrical world view wouldn’t have promised such resilience; and the days and nights seemed to press hard on his gaunt, underfed pallor.

But protecting Petty against the inimical forces through the years have been his many admirable qualities: wry detachment, a bitter-green sense of humor, understated layers of musical ingenuity, and a completely original delivery. That voice! The incomparably distinct Petty vocal is thin, top-register, nasal, and yet cured in oak barrels. No white man in America works his septum through a vowel as distinctively as Petty, except maybe Jack Nicholson on a very good day. The voice is so seductive that it’s possible to listen to Petty describe the absolute mundane quotidian and feel completely ecstatic: “It was a beautiful day, the sun beat down, I had the radio on, I was drivin’.” Most advantageous of all, the voice communicates Petty’s great subject, which is strain.

As I grew older, Petty became for me a classic-rock fave; I was always glad when the songs appeared, but didn’t habitually seek them out. And that’s why it took me a long time to notice that, over the years, Petty’s alluring vocals, plugged into the beautiful, purring engine of his band, contrasted in their bright-sized vitality with what Petty was actually saying—which was pretty near the same thing that first brought me to him as a kid. Even twenty years into his career, on his 1994 solo hit “You Don’t Know How It Feels,” the message still seemed caught in that aggrieved adolescent moment. There were, in fact, so many songs of grievance, so many songs casting unhappily inward, so many songs expressing the perpetually injured and afflicted American male. That man’s wounds are inevitably some woman’s fault. She leads him on. She keeps him waiting. She wrecks him. He knows her heart’s beyond wicked, but he can’t kick it. Yes, there’s the occasional bluesman brag: “You got lucky, babe, when I found you.” But even then, it’s all about him—and that glint of grievance. He’s sticking around to take it because taking it is what he does.

The emotions Petty describes are, of course, emotions most people experience, and to Petty’s credit, they aren’t what most people like to advertise about their inner lives. If for some the songs were awash in self-pity, many others heard the adversity in them and located something hopeful and persevering—they listened and thought, That’s me. (This was, perhaps, especially the case during breakups.) And Petty could also write excellent songs in a more romantic key, such as “Wildflowers.” Yet, in the end, so many of his memorable compositions work a path beginning with pain and leading to resentment. This is even true of “Here Comes My Girl,” in which a primary benefit of enduring love is that it enables a man feeling stuck and discouraged to “tell the whole wide world to shove it!” That thick and affirming carapace of injustice suggests that a man can subsist a long time on nothing more than his favorite grudge. As Petty writes of a man in “Rebels,” his characters are “a little rough around the edges, inside a little hollow.”

Recently, after all this time of casually going along in life to a haphazard Petty soundtrack, I decided to go hear him play. The concert I picked was in late July at the Royal Farms Arena, in Baltimore; I went with an old friend who’d played in a college jazz band and is now a doctor. When Petty took the stage, he was hidden behind shades, wearing a striking magenta shirt, a loose and colorful necktie, an amply zippered coat that he soon removed, and a vest. He had a face full of beard and, at sixty-six, his famous lank blond hair was perfect. The aroma of weed was thick enough to knock a horse into free fall, and yet, at the sight of Petty, the audience went wild. Petty spent a moment taking it in.

Petty is from Gainesville, Florida, and some consider him the Southern Springsteen. Bruce Springsteen is only a year older, and the two near-coevals are the rare figures who have successfully maintained an entire professional life span in rock and roll, the music of youth. Both had frustrated, belittling fathers, and both found escape and salvation in popular music, specifically that of Elvis Presley. Both created formidable rock bands that appeared to serve as replacement families. (A few of Springsteen’s E Streeters became very well known in their own right; Petty’s guys, too, are revered by other musicians—this is especially true of Benmont Tench, the keyboard player whom Petty met when he was twelve or thirteen, and the guitarist Mike Campbell, such a brilliantly nonchalant virtuoso that it’s possible to imagine him killing an offstage game of speed chess in between the delicious licks that are, by now, probably wired into his fingers.) Both men have worked relentlessly, and both have admitted to nearly debilitating emotional stress mid-career.

Each man left home for Los Angeles, but while Springsteen eventually returned to New Jersey to raise his family, Petty stayed out on the West Coast. (Petty is a Southerner who seems Californian, the way John Fogerty is a Californian who seems Southern.) Springsteen became a working-class hero who wrote vignettes steeped in his family’s blue-collar experience—and, as he aged, he began to advocate for those whose lives inspired his songs, charging his lyrics and his down time with political activism. Petty, on the other hand—though he’s expressed sympathy for Democratic causes, and ordered Republican candidates not to play his music from the hustings while allowing Democrats the privilege—has never seemed terribly politically engaged. For a while, he used the image of the Confederate flag onstage, only later to castigate himself for how oblivious this was, calling himself “downright stupid” for doing something that would cause many people pain.

Petty’s songs are unspecific enough that they become vulnerable to many kinds of interpretation—and there is a recurrent internal vagueness that redirects his suffering antiheroes away from the real heart of the matter and off, instead, into the great wide open. Consider Petty’s mysterious rainy-day traveller in “Running Down a Dream” next to Springsteen’s worker in “Downbound Train,” who gets laid off, loses his girl, and is now miserably employed at the car wash, “where all it ever does is rain.” Both are fine songs. One, in the way of rock anthems, creates a big, monochromatic American canvas (“It was always cold, no sunshine”). The other pointedly describes what’s led someone to feel overwhelmed and disappointed, making vivid the deep causal views of the writer.