Bob Dylan ( b27 )

 The album Down in the Groove in May 1988 sold even more poorly than his previous studio album. Michael Gray wrote: "The very title undercuts any idea that inspired work may lie within. Here was a further devaluing of the notion of a new Bob Dylan album as something significant." The critical and commercial disappointment of that album was swiftly followed by the success of the Traveling Wilburys. Dylan co-founded the band with George Harrison, Jeff Lynne, Roy Orbison and Tom Petty, and in late 1988 their multi-platinum Traveling Wilburys Vol. 1 reached three on the US albums chart, featuring songs that were described as Dylan's most accessible compositions in years. Despite Orbison's death in December 1988, the remaining four recorded a second album in May 1990 with the title Traveling Wilburys Vol. 3.

Dylan finished the decade on a critical high note with Oh Mercy produced by Daniel Lanois. Michael Gray wrote that the album was: "Attentively written, vocally distinctive, musically warm, and uncompromisingly professional, this cohesive whole is the nearest thing to a great Bob Dylan album in the 1980s." The track "Most of the Time", a lost love composition, was later prominently featured in the film High Fidelity, while "What Was It You Wanted?" has been interpreted both as a catechism and a wry comment on the expectations of critics and fans. The religious imagery of "Ring Them Bells" struck some critics as a re-affirmation of faith.

1990s

Dylan's 1990s began with Under the Red Sky (1990), an about-face from the serious Oh Mercy. It contained several apparently simple songs, including "Under the Red Sky" and "Wiggle Wiggle".

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