Willie Nelson – $25 million
How did Willie Nelson get his big break? Well, it has something to do with the release of Shotgun Willie. Born in Texas, he also made it big in the ‘70s thanks to Stardust and Red Headed Stranger. He has written a number of books, appeared in thirty movies, and advocated for the legalization of marijuana and use of biofuels. Another claim to fame of his would be the release of The IRS Tapes. The proceeds of this double-album went to the IRS and helped him pay off the tax debt that he owed.
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Willie Nelson – $25 Million