Willie Nelson – $25 million
Greatest Hits: Family Bible, On the Road Again
Willie Nelson, a songwriter, singer, and actor born in Texas, had his big break when he published Shotgun Willie. Plus, his Red Headed Stranger and Stardust albums made him an iconic figure of the 1970s. He has also starred in thirty films, written numerous books, and worked as a marijuana legalization activist and biofuel use activist. He’s also known for releasing The IRS Tapes, a double-album whose proceeds went to the IRS to pay off his unpaid tax debt.
Elton John – $500 million
Greatest Hits: Rocket Man, Crocodile Rock
To this day, rock legend Elton John has sold more than 300 million albums and had 58 Billboard singles in the top 40. In the history of the United Kingdom and the United States, his song, “Candle in the Wind,” which he wrote to honor Princess Diana after her tragic death, remains the best-selling single. He won five Grammys and several other accolades, placing him in critical success behind only The Beatles and Madonna. He is also an outstanding LGBTQ activist, raising more than $300 million for LGBTQ.