Willie Nelson – $25 Million

Willie Nelson’s contribution to country music has been immense, mainly because he is rather different than other artists of his genre. Nelson is considered to be one of the biggest artists of the outlaw country genre, because his beliefs and music didn’t match the conservative southern norm of his time.

Having earned $25 million from his music and acting portfolio, Nelson is also credited for his activism regarding the legalization of marijuana, especially for medical purposes. He’s released 73 solo studio albums, with the most recent one being the 2019 record Ride Me Back Home.