Willie Nelson – $25 million
Greatest Hits: Family Bible, On the Road Again
When Shotgun Willie was released, Willie Nelson, a songwriter, singer, and actor born in Texas, had his big break. Furthermore, 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. Also known for its release is The IRS Tapes, a double-album whose proceeds went to the IRS to pay off its unpaid tax debt.

Willie Nelson – $25 Million