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 pop-culture (and counterculture) musicians. He penned The Times They Are A’Changin'” and “Blowin’ In the Wind” Civil Rights anthems, releasing his eponymous album in the early 1960s, followed by hit record after hit. He released many albums and singles politically. He was also one of the first to use electrically amplified instruments in his rock music, a move then controversial. He sold over 100 million albums and received the Presidential Medal of Freedom and Nobel Prize in 2012 and 2016, respectively.

Bob Dylan
Brian Wilson – $75 million
Greatest Hits: Good Vibrations, I Get Around, God Only Knows, Barbara Ann
Brian Wilson co-founded Beach Boys. Signed to Capitol in 1962, he wrote over twenty-four top 40 hits for the band. He’s considered one of the most creative songwriters of the twentieth century, some saying he’s a genius. He founded Beach Boys with his brothers and cousin. Wilson still tours occasionally and is still considered indie pop and punk rock godfather. His melodies and orchestrations proved hard to initiate, though artists (including the Beatles) gained a lot from their influence.

Brian Wilson