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The Sky Is Crying is the fifth and final studio album containing performances spanning most of the career of Stevie Ray Vaughan and Double Trouble. Released about one year after Vaughan's death in 1990, the album features ten previously unreleased tracks, originally recorded between 1984 and 1989. Only one title, "Empty Arms" (complete reprisal), appeared on any of the group's previous albums. The tracks were compiled by Vaughan's brother, Jimmie Vaughan, in an effort to release the title track.
The Sky Is Crying illustrates many of Vaughan's musical influences, including songs in the style of traditional Delta blues, Texas blues, Chicago blues, jump blues, jazz blues, and Jimi Hendrix's blues-rock. The album's tone alternates primarily between uptempo pieces and gritty, slow blues. The album includes a Grammy-winning extended instrumental cover version of Jimi Hendrix's "Little Wing"; "Chitlins con Carne", a jazz instrumental; and, "Life by the Drop", a song written by Vaughan's friend Doyle Bramhall and played on a twelve-string acoustic guitar. This song is not about Vaughan's struggle with drug abuse, as many think, but actually about Vaughan's friendship with Doyle Bramhall from Bramhall's perspective.