Net Worth: $500 million
Venture: Show Dog Nashville
Toby Keith went from a popular and highly successful singer to an absolute business magnate in just a span of 25 years. Keith managed to do in just two and a half decades what most successful entertainers and businesspeople never even accomplish in their lifetimes, and created a net worth that’s equal to half a billion dollars. The legendary singer-songwriter and actor was born in Oklahoma and has been a source of pride for them ever since.
With a long list of hits that generated him a substantial income, Keith invested his newfound wealth into a business venture called Show Dog Nashville, an independent label that he currently owns. The label’s name was recently changed to Show Dog-Universal and has managed to sign a serious number of up-and-coming country artists. If you’ve never heard of Keith’s hit single “Should’ve Been a Cowboy”, you might just be missing out on one of the greatest hits of all time in the country genre.
Kenny Chesney
Net Worth: $225 million
Venture: Kenny Chesney, Inc.
With a net worth of $225 million, Kenny Chesney is a true king when it comes to creating great music that captivates a large audience of fans, then effectively monetizing that fanbase through various apparel and merchandise. The singer-songwriter and businessman have released twenty gold-certified albums so far with record-breaking success. Chesney has consistently dominated the charts with over forty Top 10 Country singles and twenty-nine of them reaching the #1 spot.
He then took that base and founded the Kenny Chesney corporation which expertly sells various items to his dedicated and loyal fans. Kenny Chesney is a singer-songwriter who has released twenty albums, nearly all of which have been gold-certified or higher by RIAA.
George Strait
Net Worth: $300 million
Venture: Codigo 1530
George Strait is your classical American country music icon. Strait is often referred to as the Clint Eastwood of country. With a career spanning over three decades, revenue from his tequila company “Codigo 1350”, and more than one hundred million album sales, this musical behemoth has built himself an impressive net worth of over $300 million.
The legendary singer is a massive critic of the modern generic style of country-pop that seeks to appeal to the largest audience, rather than focus on the genre’s tradition and background.
Reba McEntire
Net Worth: $95 million
Venture: RBI
Widely referred to as the queen of Country music, Reba McEntire is a musician and businessman that’s been around for longer than many of her male Country counterparts. The singer has dominated the genre with over thirty albums to date which almost all attained a gold status or better. She is one of the all-time best-selling Country singers and has over 75 million album sales to brag about.
Outside of her career as a musical artist, she has built a net worth of almost $100 million through smart business decisions and reinforcing and improving what’s been working for her throughout her long career. McEntire is the founder and manager of the RBI management firm and is also a successful actress.
Tim McGraw
Net Worth: $85 million
Venture: Tennessee Titans
Musical icon and owner of the Tennessee Titans NFL team, Tim McGraw is husband to the successful country artist Faith Hill. The power couple has attained the status of “rich and bestselling country musicians” with combined sales of their albums likely surpassing the 100 million mark. McGraw has released a total of fifteen albums to date that has all sold exceptionally well.
The duo has made some serious business investments using their wealth which is in the tens of millions of dollars. Their main investment was in the Tennessee Titans, as both are currently owners of the successful NFL team.