Although Roy Orbison is sometimes called the "last rockabilly singer," he might also be considered the first rock musician, who invested a fading genre with new life. Orbison played with several western swing bands in high school but he thought a musical career was a long shot and determined to pursue a more practical vocation. He enrolled in college but found he couldn't give up on music, so he put together a band and headed for Memphis to try his luck. Orbison successfully auditioned for Sam Phillips and made several records on the Sun label, but he had only one modest national hit. Success as a rockabilly star seemed to elude him, so he began to focus on songwriting. He developed a relationship with Acuff-Rose Music in Nashville and wrote a number of successful songs for acts like the Everly Brothers and Jerry Lee Lewis. In 1960 he brought a song he'd written to Don and Phil Everly for their approval; after hearing it they convinced Orbison that he should record it himself. "Only the Lonely" went to number two on the charts and established Orbison as a unique voice in rock music. His songs were poetic and lyrical, and despite their naked expressiveness they were never saccharine or trite. His quasi-operatic vocal tone, three-octave range, and melodramatic style of delivery was unprecedented in American popular music, and earned him a legion of devoted fans; Bruce Springsteen has praised the effectiveness of his "ethereal spirit voice," and Elvis Presley believed him to be the "greatest singer in the world." Though he specialized in ballads, Orbison was also capable of delivering straight-ahead rhythm and blues, which he colored with his trademark "purr."
His songs expanded the possibilities of rock and roll, and nearly every serious lyricist of the 1960s cited him as an influence. He was unable to sustain mainstream popularity and vanished from the American charts after 1967, though he continued to have hit records in Europe and Asia. In the 1980s he surprised the musical establishment with a comeback of then-unprecedented proportions; collaborations with Emmylou Harris and k.d. lang earned him Grammy awards and gold records, and after a popular Cinemax concert special he emerged with new band, the Traveling Wilburys, composed of Tom Petty, George Harrison, Bob Dylan, and Jeff Lynne of the ELO. The Traveling Wilburys' first album went to number three on the charts and yielded two hit singles, though Orbison died of a heart attack only a few weeks after its release.
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Elvis Presley, Johnny Cash
Must Haves:
 "Oh, Pretty Woman"
"Crying"
"Mean Woman Blues"
"In Dreams"
Bruce Springsteen, Chris Isaak, Gene Pitney, Don McLean, the Beatles, Bob Dylan
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