Willie Nelson – $25 million
Greatest Hits: Family Bible, On the Road Again
Willie Nelson, a Texas-born songwriter, singer, and actor, had his big break when Shotgun Willie was published. Plus, his albums Red Headed Stranger and Stardust made him an iconic 1970s figure. He has also starred in thirty films, written numerous books, and worked as an activist for the legalization of marijuana and the use of biofuels. The IRS Tapes, a double-album whose proceeds went to the IRS to pay off its unpaid tax debt, is also known for its release.

Willie Nelson – $25 Million
Elton John – $500 million
Greatest Hits: Rocket Man, Crocodile Rock
Elton John, the rock legend, has sold over 300 million albums and had 58 Billboard singles in the top 40. His song, ‘Candle in the Wind,’ which he wrote to honor Princess Diana after her tragic death, remains the best-selling single in the United Kingdom and the United States’ history. He won five Grammys and several other accolades, placing him behind only The Beatles and Madonna in critical success. He is also an excellent LGBTQ activist, raising over $300 million for LGBTQ people.

Elton John – $500 Million