Roy Orbison’s single “Oh, Pretty Woman” was released in August 1964.It spent three weeks at the top of the US’s Billboard Hot 100.It was the second and final number one single by Orbison on the US charts. In the UK, the single was Orbison’s third single to reach number one, and it also held the top spot for three weeks there.
The song title was inspired by an incident involving Orbison’s wife, Claudette. Claudette said that she was going shopping. Orbison asked her if she had enough cash. Bill Dees, Orbison’s song writing partner, quipped: “A pretty woman never needs any money.” Orbison divorced Claudette in November 1964 on account of her having an affair while he was touring the “Oh Pretty Woman” single. They were reconciled 10 months later.
The so-called British Invasion, which started around 1964–65, caused most performers of Orbison’s generation to drop off the charts. The beginning of Orbison’s career decline was also the onset of a series of personal tragedies. Having remarried in December 1966, Orbison and Claudette indulged their shared love of motorbikes. On June 6, 1966, a pickup truck pulled out in front of Claudette’s motorbike. She died instantly. On 14 September 1968, a mere two years later, Orbison’s oldest two sons died when his Nashville home burnt down.
The 1970s were not kind to Roy Orbison’s career. His LPs and singles failed to make inroads on the charts, except for a few singles in Australia. Nonetheless, Orbison’s influence was acknowledged by a new generation of performers. Artists from Gram Parsons to Nazareth to Linda Ronstadt covered his songs. Notably, the first verse of Thunder Road, the opening track of Bruce Springsteen’s breakthrough album, Born to Run, includes the couplet: “Roy Orbison singing for the lonely/ Hey, that’s me, and I want you only”.
The 1980s saw Orbison reclaiming his popularity, particularly after David Lynch’s used “In Dreams” in the movie Blue Velvet (1986). In 1987, Orbison was inducted into both the Rock and Roll Hall of Fame and the Nashville Songwriters Hall of Fame. In the same year, Bruce Springsteen, who inducted Orbison into the Rock and Roll Hall of Fame, initiated the filming of a Roy Orbison concert at Los Angeles’s Cocoanut Grove nightclub. Here, Orbison was backed by Elvis Presley’s TCB (Taking Care of Business) Band with special guests including Springsteen, Tom Waits, Bonnie Raitt, Elvis Costello, Jackson Browne, and KD Lang.
The morning after the one-off concert, a 5.9 magnitude earthquake struck Los Angeles. Several chandeliers fell from the roof of the venue and landed on the master recordings of the performance. Fortunately, the tapes were unscathed. Filmed entirely in black and white, the concert was broadcast on Cinemax on January 3, 1988. After the broadcast, the concert was released on video and on the new Laserdisc format. A live album was released in 1989.
A few months after inducting Orbison into the Rock and Roll Hall of Fame, Bruce Springsteen initiated the filming of a Roy Orbison concert at the Cocoanut Grove nightclub in Los Angeles. Here, Orbison was backed by Elvis Presley's TCB (Taking Care of Business) Band with special guests including Springsteen, Tom Waits, Bonnie Raitt, Elvis Costello, Jackson Browne, and KD Lang. The morning after the concert, a 5.9 magnitude earthquake struck Los Angeles. Several chandeliers in the ballroom fell on the master film and videotapes. After the wreckage was cleared it was determined that no damage was done.
Filmed entirely in black and white, the concert was broadcast on Cinemax on January 3, 1988 . The concert was later released on VHS and Laserdisc and a live album was released in 1989.
Thanks to stellar performances from all involved, the album is a highpoint of Roy Orbison's illustrious career. Another late-career highlight was performing and recording as The Travelling Wilburys with Jeff Lynne, Tom Petty, and Bob Dylan in 1988.
Roy Orbison died of a heart attack at the age of 52, at his mother's house, on December 4, 1988. He posthumously won the 1991 Grammy Award for Best Male Pop Vocal Performance for his live recording of "Oh Pretty Woman" on the television special Roy Orbison and Friends, A Black and White Night.