Willie Nelson | Singer-Songwriter and Author | $25 Million

There are many reasons why Willie Nelson is considered a national treasure. Aside from being one of the most prolific musicians in the United States, he also pioneered the country subgenre “outlaw country”. He is recognized by many for his talent, as well as for the colorful life he has led. Nelson is a “legend” in many ways, including weathering a few challenges along his career path.

Just take the 1992 double album, The IRS Tapes: Who’ll Buy My Memories. The album won critical acclaim and also helped him with investment planning that helped boost his fortune following a period of financial difficulties. Of course, prior to the album, his previous ones also received critical success, such as the 1973 Shotgun Willie, 1975 Red Headed Stranger, and Stardust, released in 1978. His singles Funny How Time Slips Away, Hello Walls, Pretty Paper, and Crazy are just some of his written songs that later became country music’s standards.