Jimmy Webb – $10 million
Greatest Hits: Wichita Lineman, MacArthur Park
Songwriter Jimmy Webb, born in Oklahoma, was inducted into the 1986 Songwriters Hall of Fame and the Hall of Fame of Nashville Songwriters. He has had platinum hits like “Wichita Lineman,” “All I Know,” “MacArthur Park,” and more. He has worked with big names like Linda Ronstadt and Art Garfunkel. Webb addressed his career in songwriting and shared his passion for the kind of music he aspires to, saying it was a kind of “crushed lonely hearts.” In 2017, to critical acclaim, he published his memoirs, The Cake and the Storm.
Merle Haggard – $40 million
Greatest Hits: Okie from Muskogee, The Fightin’ Side of Me
As well as the Bakersfield sound, Merle Haggard is considered one of the country genre’s founding fathers. Born in California during the Great Depression, he finally embarked on a career in country music after his father died. With songs about the working class, American patriotism, the Vietnam War, and more, his songs became popular, and he was able to turn his life around. He had thirty-eight numbers, one hit on the country charts, and some even crossed the Billboard charts.