9. Bob Dylan ($200 million)
Another legend who is surely worth a mention on this list is Bob Dylan. Famous for songs like The Times, They Are A’Changin’, and Blowin’ in the Wind, Dylan is a prominent figure in the counterculture movement of America as well as the Civil Rights movement.
Dylan’s music is mostly political. He was also one of the first singers to use an electric guitar, which many considered to be a scandal at the time.
Bob Dylan has sold over 100 million albums and is a huge icon worldwide.