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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. 1990's Welcome to the St. James Club and 1991's Curves Ahead both topped the contemporary jazz best-seller charts, and 1992's Weekend in Monaco was also a popular release. By 1993, the Rippingtons had solidified into a steady six-piece group including Freeman, Dave Kochanski on keyboards, Jeff Kashiwa on saxophone, Kim Stone on bass, Tony Morales on drums, and Steve Reid on percussion. That year saw the release of Live in L.A. In 1994, Freeman teamed with old partner David Benoit for The Benoit/Freeman Project and later in the year came Sahara, which altered the band's billing from "The Rippingtons Featuring Russ Freeman" to "Russ Freeman & The Rippingtons." In 1995, Freeman released a solo Christmas album, Holiday, followed by the eighth Rippingtons album, Brave New World, in 1995.