Orbison began singing in a rockabilly and country-and-western band in high school. He was contracted by Sam Phillips of Sun Records in 1956, but enjoyed his greatest success with Monument Records. From 1960 to 1966, 22 of his singles reached the Billboard Top 40, and he wrote or co-wrote almost all that entered the Top 10, including "Only the Lonely" (1960), "Running Scared" (1961), "Crying" (1961), "In Dreams" (1963), and "Oh, Pretty Woman" (1964). From the mid-1960s he suffered a number of personal tragedies and his career faltered amidst declining record sales.
In the 1980s, Orbison experienced a resurgence in popularity following the success of several cover versions of his songs. In 1988, he co-founded the Traveling Wilburys, a rock supergroup with George Harrison, Bob Dylan, Tom Petty, and Jeff Lynne. Orbison died of a heart attack in December that year at age 52. One month later, his song "You Got It" (1989) was released as a solo single and became his first hit to reach the U.S. Top 10 in nearly 25 years.
Orbison's honors include inductions into the Rock and Roll Hall of Fame and Nashville Songwriters Hall of Fame in 1987, the Songwriters Hall of Fame in 1989, and the Musicians Hall of Fame and Museum in 2014. 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 him at number 74 in the Top 600 recording artists.