Roy OrbisonTom Waits may have said it best.

“To me, his voice sounds like the wind forming words and being sent to you from across time. There is something so tender, so private about his voice, it confides feelings you keep mostly to yourself.” 

That voice ? and indeed the very essence of Roy Orbison ? continues to evoke similar eloquence from all those who knew him. From Bruce Springsteen to Bono, from Dolly Parton to Bonnie Raitt, those whose paths brought them into Orbison’s special orbit speak of his mystique, his humility, and his ethereal presence. Those qualities also comprised the backbone of Orbison’s artistry. Two decades after his death, he remains one of the most authentic artists rock and roll has ever produced. 

Orbison’s story is one of triumph and tragedy. By the time he cut his first single, “Ooby Dooby,” in May of 1956 at Sun Studios, he was already a veteran musician. As his son Roy Orbison Jr. recently pointed out, on “Ooby Dooby” Orbison unleashed two “in-your-face” guitar solos at speeds previously unheard of at Sun. His time at the label was short-lived, but while he was there he forged enduring friendships with Johnny Cash and Elvis Presley. He also scored his first commercial success ? a song titled “Claudette,” inspired by his first wife – that the Everly Brothers had a hit with in 1958. 

Orbison left Sun for a brief stint at RCA before signing to the fledgling Monument Records label in mid 1959. While there, his career took flight. From 1960 to 1965, “Only the Lonely,” “Crying,” “Candy Man,” “In Dreams” and other hits propelled him to mainstream heights. He was the only American rock artist to chart regularly during the British Invasion, and fittingly, he toured with the Beatles in 1963 and with the Rolling Stones in 1965. 

The crowning achievement during this period was “Oh, Pretty Woman.” Composed on a 12-string Epiphone acoustic, the 1964 classic has since become part of the rock and roll (and film) lexicon. It’s a safe bet that no other piece of American culture has furthered the careers of both Eddie Van Halen and Julia Roberts. And, as every aspiring six-string artist knows, few songs have boasted as memorable guitar riff. 

A lesser-known song from this period, “Ride Away,” highlighted Orbison’s love of motorcycles. His affection for two-wheelers was decimated, however, when on a summer day in 1966 his beloved wife, Claudette, was struck and killed as she and Orbison were cycling together. Two years later, on Sept. 14, 1968, tragedy struck again when, horrifically, two of his three sons lost their lives in a house fire. Roy Dwayne Orbison was 10 years old; his brother, Anthony, was just six. Unable to write songs in the wake of such crushing loss, Orbison nonetheless continued to tour, seeking solace in music and in the support of fans.

In later years Orbison often said, in interviews, “Barbara saved my life.” The woman he was speaking about became his wife in 1969, and together the two worked through a lengthy period during which Orbison grieved, devoted himself to his new family, and regained his creative footing. Even so, these so-called “lost years” were hardly a fallow time. By the end of the '70s Orbison had recorded a Grammy-winning duet with Emmylou Harris (“That Lovin’ You Feelin’ Again”), had toured with the Eagles, and had participated in Farm Aid and other benefit shows.

The '80s kicked off with renewed interest in Orbison. Van Halen’s flashy re-working of “Oh, Pretty Woman,” plus covers by Linda Ronstadt and Don McLean (of “Blue Bayou” and “Crying,” respectively) spotlighted Orbison’s prowess as a master songwriter. In 1985, Orbison reunited with former Sun labelmates Carl Perkins, Johnny Cash and Jerry Lee Lewis for an album titled Homecoming. A year later, in 1986, filmmaker David Lynch tapped into Orbison’s mystique by making “In Dreams” the centerpiece of his cult classic, “Blue Velvet.”

The last two years of Orbison’s life were among his most productive. Conceived and produced by Orbison's wife Barbara and musical director T-Bone Burnett, the 1987 performance film, Roy Orbison and Friends: A Black & White Night, remains one of the greatest concert films ever produced. A palpable love for Orbison emanated from the assembled greats who came to pay tribute. Joining Orbison on-stage, in addition to Burnett, were Bruce Springsteen, Tom Waits, Elvis Costello, Jackson Browne, J.D. Souther, Steve Soles, k.d. lang, Jennifer Warnes, and Bonnie Raitt, as well as former Sun Records session icons Glen D. Hardin and James Burton. Filmed in soft black and white, the concert brims with surreal power.

Shortly after filming Black & White Night, Orbison, Jeff Lynne, George Harrison, Tom Petty and Bob Dylan formed their impromptu dream group, the Traveling Wilburys. Determined not to take themselves too seriously, the ramshackle gang nonetheless crafted a superb, Grammy-winning album. Fast on its heels came Mystery Girl, the Orbison solo album that would prove to be his last. Released posthumously in February 1989, the album became the biggest seller of Orbison’s career, peaking at No. 5 on the Billboard 200 chart.

Roy Orbison died of a heart attack on December 6, 1988. He was just 52 years old, but his spirit seemed far older and wiser than his chronological age. Twenty years after his death, his impact continues to reverberate in all quarters of our culture. Filmmakers seek out his songs, singers still cover them, and his peers continue to extol his virtues as both an artist and a man.

“I’ll always remember what he means to me and what he meant to me when I was young and afraid to love,” said Bruce Springsteen, during the 1987 induction of Orbison into the Rock and Roll Hall of Fame. “In 1975, when I went into the studio to record Born to Run, I wanted to make a record with words like Bob Dylan, that sounded like Phil Spector’s production, but most of all, I wanted to sing like Roy Orbison. Now, everybody knows that nobody sings like Roy Orbison.”