At 15, Phoenix returned to her roots in music and formed the band Aleka's Attic with her then 17-year-old brother River. River, along with bass player Josh McKay, wrote music and lyrics and Rain sang backup. The band secured gigs in and around their home town of Gainesville, Florida By this time, River's career had taken off and so the band was often put on hold for River's demanding schedule. In 1988, Aleka's Attic were signed to a development deal with Island Records and in 1989 released the track "Across The Way" on a benefit album for the animal rights group PETA. In 1991, they made a tour of east coast clubs and colleges. At this time, Phoenix joined her brother River on the set of his tenth movie, My Own Private Idaho. She met Director Gus Van Sant to whom River suggested she would be perfect for a role in his upcoming project, a film adaptation of Tom Robbins's cult novel, Even Cowgirls Get the Blues. She was cast as head cowgirl Bonanza Jellybean, alongside Uma Thurman.