Jerry Garcia – $40 million
Greatest Hits: Truckin’, Sugaree
Jerry Garcia, born in San Francisco, was part of the popular band throughout his thirty-year career. He also had several other bands and other solo albums. He was 13th on Rolling Stone’s “100 Greatest Guitarists” list. He was Grateful Dead’s main songwriter, best known for his psychedelic rock style. One of Warner Records’ biggest hits was “Truckin’,” which made its first appearance on Dead’s album, American Beauty. He was known for his improvisation and guitar solos, which suited him well because, he said in an interview, it relieved stress.

Jerry Garcia
Paul Simon – $75 million
Greatest Hits: Bridge Over Troubled Water
Paul Simon wrote nearly all songs, including “Mrs. Robinson,” “Sound of Silence,” and perhaps their most popular hit, “Bridge Over Troubled Water,” Columbia Records owned. The duo broke up in 1970, and Simon published Graceland, influenced by South Africa, where he lived for a while. On his release, Graceland sold 14 million copies, and it’s his most successful solo work to date. He had a Broadway career, writing musicals. He wrote The Capeman with poet Derek Walcott. He was a screenwriter.

Paul Simon