Willie Nelson – $25 million
Greatest Hits: On the Road Again, Family Bible
The Texan-born Willie Nelson would become a highly regarded artist, singer, and songwriter when unleashed Shotgun Willie. The Stardust and Red Headed Stranger albums would make him a real celebrity in the 1970s. Nelson is also famous for his love of marijuana and his advocacy for its legalization. He is also an author and prolific actor with more than 30 movies under his belt. After dodging his taxes for many years, Nelson finally wrote the IRS Tapes to cover his huge debt with a double-album recuperation.
Willie Nelson
Elton John – $500 million
Greatest Hits: Crocodile Rock, Rocket Man
Elton John enjoyed record sales of over 300 million units, and 58 entries into the top 40 with his many Billboard singles. The United States and the United Kingdom were rocked by the emotive tribute song called Candle in the Wind, which he wrote for Princess Diana when she tragically lost her life. He has five Grammy awards, and many other titles, which makes him one of the most successful artists topped only by fellow greats like Madonna and The Beatles. John is committed to his LGBTQ+ advocacy, having funded over $300 million in related charity efforts.
Elton John
