Bob Dylan ($200 million)
Despite his early preached ideologies about wealth and accessibility during the folk revolution in the ‘60s, Bob Dylan has accrued a significant amount of money over the years. Dylan defied many conventions of the era, constantly changing the design and format of his music, which infuriated a lot of his fans. Over time, Bob Dylan fell into a rhythm, and he started to release music as expected by his fans, skyrocketing him into a high earnings category in the music industry. Due to Dylan’s legacy, he has been able to collect a serious amount of cash during his career, $200 million worth of it to be specific.