Naomi Judd ($25 million)
We have already talked about Wynonna Judd, so let us focus on her mother now. As the Judds, they won over many people and took home five Grammys. Suddenly, the group disbanded after she found out that she had Hepatitis C. In 1991, she decided to stop performing because of the chronic condition.
Cole Swindell ($3 million)
Before he made his own music, Cole Swindell wrote songs for the likes of Scotty McCreery, Thomas Rhett, and Luke Bryan. In 2014, he released his first solo album and followed it up with a second one two years later. We can’t help but sing when “Chillin’ It” and “Hope You Get Lonely Tonight” comes on!