1988 was Roy Orbison's big year. It started with Cinemax special, A Black and White Night, which aired in January. A diverse set of artists, including Tom Waits, Elvis Costello, Bonnie Raitt and Bruce Springsteen, formed an all-star band, backing the man who perfected the art of the rock power ballad.
Orbison started out as a Sun rocker. After shifting to the nascent Monument label in the early 1960s, he had a long string of hits -- "Pretty Woman," "Only the Lonely," and "In Dreams" among them -- but personal tragedies put an end to that. His wife Claudette (Orbison wrote a song about her recorded by the Everly Brothers) was killed in a motorcycle accident in 1966, and his two sons died in a fire three years later. In the 1970s, he experienced health problems and underwent triple bypass surgery.
By then, Orbison had faded into the background, though he never stopped working. Covers by Linda Ronstadt ("Blue Bayou") and Van Halen ("Pretty Woman") revived interest. Then came appearances on the soundtracks for Roadie, Hiding Out (he and k.d. lang dueted on "Crying") and most importantly Blue Velvet. The Cinemax special aired to great acclaim, and Orbison began working with Jeff Lynne on a comeback album.
Lynne was also producing George Harrison and thought Harrison and Orbison should record together. He booked time at Bob Dylan's studio, and on the way there, the three men stopped by Tom Petty's house and invited him to join the group. Dylan made it five. They recorded their first song, "Handle with Care," and decided to do more. The quintet named themselves the Traveling Wilburys, Orbison adopting the alias Lefty Wilbury, after Lefty Frizzell. The Traveling Wilburys' self-titled debut album was released in October 1988 and was an immediate hit, becoming Orbison's most successful record since his glory days. The Lynne-produced solo record, it was promised, would be Orbison's biggest album ever.
On December 6, as Roy Orbison's magic year of 1988 was coming to an end, he suffered a fatal heart attack. He was just 52 years old. In Martin Scorcese's HBO documentary about George Harrison, Tom Petty recalls getting a call from the ex-Beatle to tell him Orbison had passed. "Aren’t you glad," Harrison asked Petty, "it’s not you?"