Guitarist Russ Freeman originally conceived of the Rippingtons as a changing lineup of strong contemporary jazz musicians. After releasing his debut solo album, Nocturnal Playground, in 1985, Freeman assembled the first version of the band, which featured David Benoit on piano and Brandon Fields, Dave Koz, and Kenny G on saxophones, for the appropriately titled Moonlighting (1986). Kilimanjaro, the first Rippingtons album to break into the pop charts, followed in 1988. As of 1989's Tourist in Paradise, the group was contracted to the GRP label.
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