It’s 2:00 P.M. at the twenty-fifth annual Roy Orbison Festival in Wink, Texas, and everyone is wilting in the afternoon heat. There are maybe two dozen people here at festival central, a parking lot on Wink’s main street. A food truck sells brisket burritos and giant plastic cups of lemonade; a few vendors are set up under portable tents, hawking patterned sundresses, hand-painted wooden crosses, cheap jewelry. I say some small-talk words about the weather to a man selling belly-button rings and anti-Obama bumper stickers. “I don’t mind it,” he says placidly, his hands on his belly. “Don’t mind the cold, neither.” The ground is littered with the remnants of an epic silly string battle. Someone’s got a boom box turned up as loud as it will go, tuned to a top-forty country station out of Pecos. Other than his name on a stack of official t-shirts, there’s no evidence that the Roy Orbison Festival has anything to do with Roy Orbison at all. 

Getting to Wink, the tiny windswept town not far from the Texas–New Mexico border where Orbison grew up, requires a long drive through desert scrubland, the monotony of the landscape interrupted by only the occasional cow or oil derrick. As in much of West Texas, the land is empty but owned, and therefore off-limits. Nearby highlights include Kermit, “the only town in Texas to be named after one of Theodore Roosevelt’s sons,” and the world’s largest stand of Havard oaks, which turns out to be a thirsty cluster of desert-stunted, knee-high trees. This is what passes for a forest in West Texas, “the center of everything, five hundred miles from anything,” as Orbison once put it.

The Orbison family moved to Wink in 1946, when Roy was ten years old, so his father, Orbie Lee, could find work in the oil fields. Though he did eventually get hired on as a rigger, the Orbisons were late to the oil boom party: Wink’s population peaked at around 6,000 in 1929; seventeen years later, when the Orbisons settled in, most of the wells had dried up and the town had shrunk to about 1,500 residents. “It was macho guys working in the oil field, and football, and oil and grease and sand and being a stud and being cool,” Orbison said later. “It was tough as could be, but no illusions, you know? No mysteries in Wink.”

Orbison wasn’t popular; later he said he felt “totally anonymous, even at home.” He started wearing glasses at age four. When he tried out for the Wink Kittens, the junior high version of the Wink Wildcats high school football team, the helmets didn’t have face guards, and his glasses kept falling off. He didn’t make the team. 

Growing up is a lonely enterprise, even more so in a town that’s past its prime. Once he made his money, Orbison left for Tennessee, then Malibu. He wasn’t one to rhapsodize about his childhood very often, but once I visited his hometown, I couldn’t help but hear a telltale hint of Wink every time I listened to his songs: that sense of missing out, of having been passed by. An absence, a longing, a loneliness.

One of the most striking things about Orbison was the mismatch between his voice and the body it came out of. His range spanned three octaves; listening to him tremble and bellow and emote, you got the sense there was nothing his voice couldn’t do. His singing sounded, Dwight Yoakam once said, like “the cry of an angel falling backward through an open window.” Just listen to that crescendo at the end of “Crying.” Never has a song about romantic despair sounded quite so triumphant in its heartbreak.

But in person, Orbison was weak-chinned and scrawny (and, later, weak-chinned and doughy), with an indoor-kid pallor. There were persistent, false rumors that he was albino, or that he wore dark glasses because he was blind. Growing up, he was self-conscious about his hair, which was so pale it appeared white. In high school, he began dyeing it black and gelling it into a stiff pompadour, which only made his appearance more uncanny. In contrast to his contemporaries who danced and capered onstage, Orbison stood stock still, barely moving more than he had to. It’s no wonder that David Lynch is a fan. It’s also no surprise that record producers were cautious about taking a chance on him. “I knew his voice was pure gold,” said Sun Records producer Sam Phillips, who recorded Orbison’s band the Teen Kings in the late 1950s. “I also knew if anyone got a look at him, he’d be dead inside a week.” 

I got my first pair of glasses when I was seven. They were beautiful, with round plastic frames the color of pink lemonade. Over the next few years, my eyesight continued to degenerate rapidly enough that I started seeing a specialist. I remember those early years at the eye doctor as strangely soothing: the comfortable routine of the big-E vision chart, the low light of the examination room, the Phoroptor machine’s cool metal on my forehead as the nurse toggled between lenses: Which looks clearer to you, A [flip] or B? Unlike other doctors, who diagnosed what was wrong with you, the eye doctor adjusted the world to suit your particular needs, manipulating everything into better focus. 

But over the years, my eyes continued to worsen, and the tests they required got more invasive and uncomfortable: numbing drops, a blinding blue circle of light, the dreaded pressure-testing instrument that pushed against my eyeball, causing me to irrationally worry that it might pop. By age sixteen, my eyes were worse than my father’s, a man so nearsighted he was nicknamed “Mole” for how squinty and helpless he seemed when he didn’t have his glasses on. In my twenties, my lenses were thick enough that strangers in the grocery store saw fit to remark on them. I started carrying a copy of my prescription in my wallet as a hedge against times when I’d meet people who thought they had bad vision. I’d ask about their refraction, and they’d proudly offer some pathetic number: -5.25, -7.75, -4. I’d scoff and brandish my documentation: I’m -15 in the right, -15.25 in the left.

Unlike Roy Orbison, I was never bullied for my glasses—I just felt ignored. During my brief, disappointing experiment with contact lenses, no one recognized me; having to look me directly in the eyes seemed to confuse them. They were used to seeing my glasses instead of my face, I suppose. In high school, Orbison himself refused to date the glasses-wearing girls his friends set him up with. I resent this, even as I also understand it. For a long time, I was the same way. I saw thick glasses as a visible marker of difference, and of weakness. I didn’t consider that they could be the opposite as well.

Many people have the vague idea that Roy Orbison’s life was marked by tragedy, and that was why he hid his eyes behind dark glasses and sang so many songs about crying, feeling afraid, and dreaming of happier times. This actually gets the cause-and-effect sequence of Orbison’s life all wrong. It turns out that he wrote those terribly sad songs first, then he started dressing in black, and only later did his life fall apart.

Orbison recorded most of the songs he’s known for between 1960 (“Only the Lonely”) and 1964 (“Oh, Pretty Woman”). Although many were pop hits, in retrospect they’re so strange as to be almost alarming, because of his remarkable voice and the unconventional song structures he gravitated toward, but also thanks to what he chose to sing about: operatic expressions of terror and grief; desire imbued with tragedy; and always the preoccupation with crying and dreaming and pain. This was pop music that was best listened to, according to Bruce Springsteen, “alone and in the dark.” 

It wasn’t until the end of his most successful period that Orbison first performed in the dark glasses that would become his trademark—he left his regular pair on a plane and so had to perform in prescription sunglasses instead. The all-black outfits followed, solidifying the impression of Orbison as a man who performed his insecurity and alienation onstage in front of thousands of fans. Before long, the glasses became central to Orbison’s persona; while his earliest album covers featured Orbison posing with a car or guitar, 1965’s Orbisongs depicts Orbison’s dark glasses resting on top of sheet music. The metonym had taken hold; the glasses had replaced the face.

Orbison didn’t get to rule the charts for long. By the mid-1960s, the British Invasion made Orbison seem old and obsolete before he’d even turned thirty. On tour with Orbison and the Rolling Stones in 1965, Marianne Faithfull recalled him as “large and strange and mournful looking, like a prodigal mole in Tony Lama cowboy boots.” One night, Faithfull convinced Orbison to let her try on his glasses. A photographer captured the moment: Faithfull peeks over the frames like a coy librarian; next to her, absent his signature Ray-Bans, Orbison’s face looks naked, his smile frozen halfway between pleasure and terror.

One year later, Orbison’s wife Claudette was killed in a motorcycle accident; two years after that, in 1968, two of their young sons died in a fire that also destroyed their home. Orbison’s older brother, once a star player on the Wink Wildcats football team, died in a drunk driving accident in 1973. Orbison’s career entered a period of eclipse. He was stuck in a punishing record contract, required to release more and more albums that sold fewer and fewer copies. He made half-hearted attempts to connect with a fan base whose tastes were evolving, covering the Bee Gees, popping up on Dukes of Hazzard, reprising “Pretty Woman” in an ad for Sasson jeans. He gave up his pompadour for a Beatles-inspired bowl cut, then grew a ponytail. None of it made much of a difference.

“As the Sixties turned into the Seventies I didn’t hear a whole lot I could relate to,” he said later. “So I kind of stood there like a tree where the winds blow and the seasons change and you’re still there and you bloom again. With time.”

Wink’s Roy Orbison Museum has exactly one room and is luxuriously air-conditioned. It takes about ten minutes to see everything, including Roy’s high school yearbooks—“To lead a western band / Is his after school wish / And of course to marry / A beautiful dish”—and the faded photographs of the Wink dance hall where the Teen Kings once played. A large world map is dotted with colored pins, showing how far visitors have come to pay homage to Orbison: dozens from the UK, one from Mali, a handful from Australia. I take another loop around the room, looking for an excuse to postpone going back outside.

“Do you want to see his glasses?” the small woman behind the counter asks. I turn toward her, confused, as she removes a black case from a shelf and snaps it open. Inside is a pair of glasses. They have solid black frames and thick, violet-tinted lenses. The woman explains that Orbison’s second wife, Barbara, donated them to the museum after he died. “Try them on,” the woman urges. “Take a picture with them, if you like.”

I take off my own glasses, then gingerly unfold Orbison’s. They are surprisingly heavy—old enough, perhaps, that the lenses are made of real glass, rather than some fancy, lightweight polycarbonate. I hesitate for a second: There is something very personal about wearing someone else’s glasses, and I worry that I’m intruding on something—what, though, I’m not entirely sure. When I do finally put them on, the world looks fuzzy, but in a different way than I’m used to. I can’t tell if that means my eyes are worse than his, or that his were much worse than mine. I’m not sure it matters; we’re both certainly members of the thick-glasses tribe. In the photograph my boyfriend took of that moment, my magnified eyes are anime-character huge. The frames are awkwardly big on me, but I have a dreamy look on my face, as if I’m looking at something wonderful that no one else can see.

As music scholar Peter Lehman has pointed out, many Orbison songs take place in the moment between waking and sleep, that drifting place where it’s difficult to distinguish dreams from reality. A sad childhood in a declining desert oil town might have made Orbison dreamy, but I bet his bad eyes did it too. If the first thing you do in the morning is reach for your glasses, it doesn’t take long to learn that the apparent solidity of the world is something of an illusion. 

Even though he had every excuse to do so, Orbison never really fell apart. He didn’t like the taste of alcohol, never developed a serious drug habit. He was religious, but in a mild, consistent way, without any of Johnny Cash’s ardor and despair. There’s very little that’s glamorous about Orbison; the grandfatherly things he loved when he was twenty-five were the same things he loved when he was fifty: candy bars, model airplane kits, books about World War II, fast old cars. 

Orbison didn’t have an easy life, for reasons of both temperament and circumstance, but that never made him bitter or despairing. Instead, he found a way to root down into the things that made him strange—that dreaminess, isolation, and pervasive sense of fear—and pull an inexplicable power from them. He needed his glasses, in more ways than one.

Orbison died young, of a heart attack at fifty-two, but not before making a remarkable comeback. In the years before his death, he was inducted into the Rock and Roll Hall of Fame, joined the Traveling Wilburys, befriended David Lynch, and landed a new record contract. The album he was working on at the time of his death ended up selling better than anything else he’d ever released, and he became the only artist since Elvis to have two albums posthumously in the Billboard Top 5 at the same time. Days before his death, he was still amazed by it all: “My life,” he said, “is a never-ending dream.”

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