6. Willie Nelson

Willie is an American country music singer-songwriter, author, poet, actor, and activist.

The success of the album Shotgun Willie (1973), combined with the commercial success of Red Headed Stranger (1975) and Stardust (1978), made Nelson one of the most recognized artists in country music.

However, his huge success and wealth lasted until 1990 when Willie declared bankruptcy, owing the IRS $16.7 million in unpaid back taxes and fees.

There have been a lot of speculations on how exactly he went broke. One story says his accountants had not paid Willie’s taxes for years, the other states they had invested his money in tax shelters that turned out to be illegal.

To help pay off his tax evasion debt, in 1991 Nelson released an album symbolically titled “The IRS Tapes: Who’ll Buy My Memories,” and it paid off, since he managed to pay all of his debts to the government. He also had to auction off some of his memorabilia, and by 1993 he had finished paying the IRS all the tax he owed.

So, even when he thought that all was lost and there was no way out, Willie turned to the one thing he knew will never let him down – his music, and the music reached out. Awesome.