Pilgrim

Eric Clapton later revealed that his intention for 1998’s Pilgrim was “to make the saddest record of all time.” The album addresses the two losses that cast a shadow on all of Clapton's post-'80s music: the 1985 death of the father he'd never met and the accidental 1991 death of his four-year-old son. These two tragedies are connected in “My Father’s Eyes,” a confession and elegy disguised in a midtempo gospel pop structure. In “Circus,” the other keystone song here, Clapton recalls the last day he spent with his son and then turns the image of the circus into a metaphor for devastation: “And it's sad, so sad, there ain't no easy way 'round/And it's sad, so sad, all you friends gather 'round/'Cause the circus left town.” Musically, the album leans heavily on the contemporary R&B that Clapton honed after his collaboration with Babyface; it also contains traces of his burgeoning interest in dance music. The modernized programming was a turnoff for some of Clapton’s fans, but even when it’s built on mechanized beats, Pilgrim stands among the most delicate and vulnerable works of his career.