Alan Jackson (62) – $150 Million

The country music singer Alan Jackson is a cowboy-hat-wearing American classic with over 75 million records sold. Known for songs such as “Remember When,” “Country Boy,” and “Gone Country,” Jackson managed to amass a whopping $150-million fortune by staying true to the roots of the country music genre.

Often included in lists featuring the best-paid country music artists in America, Jackson is expected to continue to be successful (and very rich) in his golden years. Retirement is undoubtedly not part of the plan right now: in 2021, Jackson performed in the “National Memorial Day Concert” and appeared in “Today” and “A Capitol Fourth.”