Jerry Garcia – $40 million
Greatest Hits: Sugaree, Truckin’
The San Francisco born artist enjoyed around three decades in the music industry alongside his incredible band. The man cycled through various bands in his time, as well as enjoying plenty of albums on his own. Garcia was also a sensational guitarist, earning the 13th spot on the “100 Greatest Guitarists” list by Rolling Stones magazine. Grateful Dead fans will know Garcia for his songwriting provisions for the rock band, as well as his psychedelic rock-fueled inspirations. Truckin’ was one of the songs where his improvised guitar solos really shone, something that would allow the artist blow off some steam.
Jerry Garcia
Paul Simon – $75 million
Greatest Hit: Bridge Over Troubled Water
Paul Simon has written a monumental number of superb and timeless songs, such as Bridge Over Troubled Water, Sound of Silence, Mrs. Robinson, and so on. These songs were recorded with Columbia Records. He would eventually split up with his artist partner, Art Garfunkel, to commence his 1970 solo career. This led to the writing of Graceland, a song that was inspired by his time in South Africa. The track enjoyed 14 million record sales not long after it was published, becoming his best solo piece ever. He also enjoyed some time on Broadway where he produced several artists.
Paul Simon
