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The Sky Is Crying is the fifth and final studio album of Stevie Ray Vaughan and Double Trouble, containing recordings spanning most of their career. Released about one year after Vaughan's death in 1990, the album features ten previously unreleased tracks 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, as a vehicle for releasing the title track.
The album received mostly positive reviews. Critics praised the blues and jazz style to the album, and the solid track list to the album, but criticized the lack of original songs – a rather specious fault-finding, considering Vaughan had died before the album was even conceived.
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"; Kenny Burrell's "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.
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