Roy Kelton Orbison (April 23, 1936 – December 6, 1988) was an American singer-songwriter known for his distinctive, impassioned voice, complex song structures, and dark emotional ballads. The combination led many critics to describe his music as operatic, nicknaming him "the Caruso of Rock" and "the Big O." Between 1960 and 1964, 22 of his songs placed on the Billboard Top 40, including "Only the Lonely" (1960), "Crying" (1961), "In Dreams" (1963), and "Oh, Pretty Woman" (1964). Born in Texas, Orbison began singing in a rockabilly and country and western band in high school. He was signed by Sam Phillips, Sun Records in 1956, but his greatest success came with Monument Records in the early 1960s. While most male rock and roll performers in the 1950s and 1960s projected a defiant masculinity, many of Orbison's songs instead conveyed a quiet, almost desperate, vulnerability. His voice ranged from baritone to tenor, and music scholars have suggested that he had a three- or four-octave range. During performances, he was known for standing still and solitary, and for wearing black clothes, to match his jet black hair and dark sunglasses, which lent an air of mystery to his persona. From the late 1960s to late 1970s, Orbison was marred by a number of personal tragedies while his record sales declined. He experienced a resurgence in popularity through the success of several cover versions of his songs and the use of his 1963 song "In Dreams" in David Lynch's film Blue Velvet (1986) and his hit "Oh, Pretty Woman" as the title track to film Pretty Woman in 1990. In 1988, he co-founded the Traveling Wilburys supergroup with George Harrison, Bob Dylan, Tom Petty, and Jeff Lynne. Orbison recorded his last solo album, Mystery Girl, the same year but died of a heart attack shortly thereafter. His honors include inductions into the Rock and Roll Hall of Fame in 1987, the Nashville Songwriters Hall of Fame in the same year, and the Songwriters Hall of Fame in 1989. Rolling Stone placed him at number 37 on their list of the "Greatest Artists of All Time" and number 13 on their list of the "100 Greatest Singers of All Time'. In 2002, Billboard magazine listed Orbison at number 74 in the Top 600 recording artists.

He is also known as Roy Kelton Orbison and The Big O.

Orbison determinedly pursued his second chance at stardom, but he expressed amazement at his success: "It's very nice to be wanted again, but I still can't quite believe it." He lost some weight to fit his new image and the constant demand of touring, as well as the newer demands of making videos. In the final three months of his life, he gave Rolling Stone magazine extensive access to his daily activities; he intended to write an autobiography and wanted Martin Sheen to play him in a biopic. In November 1988, Mystery Girl was completed, and Traveling Wilburys Vol. 1 was rising up the charts. Around this time, Orbison confided in Johnny Cash that he was having chest pains and said he would have to do something about his health, but he never did. He went to Europe, was presented with an award there, and played a show in Antwerp, where footage for the video for "You Got It" was filmed. He gave several interviews a day in a hectic schedule. A few days later, a manager at a club in Boston was concerned that he looked ill, but Orbison played the show, to another standing ovation.

Orbison performed at the Front Row Theater in Highland Heights, Ohio, on December 4. Exhausted, he returned to his home in Hendersonville to rest for several days before flying again to London to film two more videos for the Traveling Wilburys. On December 6, he spent the day flying model airplanes with his sons and ate dinner at his mother's home in Hendersonville. Later that day, he died of a heart attack, at the age of 52.

The tabloid National Enquirer suggested on its cover that Orbison had worked himself to death. A memorial was held in Nashville, and another in Los Angeles; he was buried at Westwood Village Memorial Park Cemetery. On April 8, 1989, Orbison became the first deceased musician since Elvis Presley to have two albums in the US Top Five at the same time, with the Traveling Wilburys album at number 4 and his own Mystery Girl at number 5. In the United Kingdom, he achieved even greater posthumous success, with two solo albums in the Top 3 in the chart dated to February 11, 1989, Mystery Girl at number 2 and the compilation The Legendary Roy Orbison at number 3.