Jerry Garcia – $40 Million

Jerry Garcia knew how to put on a show when he played with The Grateful Dead. He was the band’s lead guitarist and vocalist, and he became famous for his distinct improvisation solos during live shows. He loved improvising, but he also had the technical capability to do so. Rolling Stone has included him in its “100 Greatest Guitarists of All Time” list.

Garcia also increased his earnings by working as a session musician and a solo artist. Having earned around $40 million after years of touring and releasing material, one would think that his life would be a fairy tale. Yet, he died in 1995, aged just 53, as he battled both diabetes and addiction to several illegal substances.