1) Toby Keith estimated $500 million
And the richest country music singer is Toby Keith. He is famous for his performance on the song “How Do You Like Me Now?!”
When he signed with DreamWorks Records Nashville in 1998, his success came immediately. The song “How do you like me now?!” it was the title track to his album of the same name, it was #1 Country Song of 2000.
The following albums were also certified multi-platinum. Years later he founded his own label Show Dog Nashville, which merged with Universal South Records and became Show Dog-Universal Music.
With more than 7 albums in his playlist, Keith had more than 40 singles on the Billboard Hot Country Songs charts.
