Recorded in 1993, Stone of Sisyphus didn't appear as scheduled in 1994 due to Chicago's record label, Warner, believing the album to be too uncommercial. As it often happens with unreleased records by major acts, a legend built up around the scrapped record, at least among devoted Chicago fans, the kind who would appreciate the musical stretching found on Stone of Sisyphus. Frankly, they may be the only group to appreciate the departures on Stone of Sisyphus, as it's a curious creature -- a splashy, expensive mainstream album that's restless yet not quite experimental but entirely devoid of pop songs. If this had been the Chicago of the early '70s, who specialized in ten-minute jazz-rock songs on their series of double albums, perhaps it would have been easier for the label to accept the variety of sounds here, but this was a Chicago coming out of five years of big placid adult contemporary hits -- songs that courted an audience that would bristle at the stiff funk of "Mah-Jong" or the Jordanaires singing harmonies on the airy "Bigger Than Elvis." Surely, any listener would shudder at "Sleeping in the Middle of the Bed," an absurd socially conscious rap track by Robert Lamm that almost certainly was the final nail in the coffin for Warner, as it's hard to imagine any audience that would find this appealing. "Sleeping in the Middle of the Bed" also goes a long way toward illustrating just how odd Stone of Sisyphus is: it's tame compared to any other record from 1993-1994, but judged alongside Chicago's other albums it's flat-out bizarre, the sound of a group desperate for a departure in the wake of a flop (1991's Chicago Twenty 1), so the bandmembers will try anything different within the confines of their sound. This means not abandoning the pristine productions -- this time courtesy of Peter Wolf, not the guy from J. Geils -- but it does mean leaving melody behind, switching up song constructions, getting a little jazzy again, and indulging a social consciousness, all things that reward the patience of loyal listeners and bewilder anybody else.
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AllMusic Review by Stephen Thomas Erlewine