Bob Dylan – $200 million
Greatest Hits: The Times, They Are A’Changin’, Blowin In The Wind
Folk singer Bob Dylan is one of the most influential pop culture artists of all time. Throughout the early 1960s, The Times They Are A’Changing ‘and’ Blowin ‘In the Wind, his eponymous album, his hit record after hit, released. Politically, many of the albums and singles he released were popular. He was among the first to use amplified instruments in rock music (in which the use of amplified instruments had previously been controversial). The artist sold over 100 million albums in 2012 and was awarded the Presidential Medal of Freedom in 2016.

Bob Dylan – $200 Million