Carrie Underwood
Net Worth: $65 million
Venture: CALIA by Carrie Underwood
When we first heard Carrie Underwood perform as a young and aspiring artist in a popular music reality show American Idol, it was clear from the start that she was going to be causing some huge vibrations in the music world. This is exactly what happened, as the Oklahoma-born singer ended up becoming one of the most successful artists from her state. Underwood would go on to win American Idol, three Grammy awards and build her brand as a highly acclaimed musical artist.
Underwood’s musical ventures and business enterprises helped her secure a serious $65 million in personal net worth. Outside of music, she is also the founder and principal investor in her clothing line, CALIA, which provides sportswear for athletes that are based on her Oklahoma roots.
Billy Joe Thomas
Net Worth: $5 million
Venture: Pepsi
As we move from Billie Jo Spears to Billy Joe Thomas, it clearly dawns why old-school fans of country have often lamented that traditional country has “just isn’t what it used to be”. The ‘60s and ‘70s produced some of the most prolific and incredible country singers to date, perhaps it was the era and the culture, or maybe it was due to the older recording quality, but either way, Billy Joe Thomas definitely stands head and shoulders above many of today’s pop-country musical counterparts with his soft and tender music that somehow manages to make your soul feel happier.
The country singer is mostly known for his musical mix of pop, country and Christian which came from his background as a church choir singer in his youth. His single, "I'm So Lonesome I Could Cry" which was a cover of the hit Hank Williams song gained over a million sales and launched Thomas' career. He has won several Grammy Awards and was recently inducted into the Grammy Hall of Fame for his iconic song, "Raindrops Keep Fallin' on My Head", which was featured in many films and video-games.
Jo Dee Messina
Net Worth: $9 million
Venture: Bigger Than This
Two-time Grammy award nominee Jo Dee Messina is a perfect example of a country singer taking the music industry in a perfect sequence of events. From a young age, Dee Messina was proving herself to be a very talented musician. She would tour her state of Massachusetts with her brother and play music in various local clubs. She was discovered eventually and signed a label deal with Curb in the early ‘90s. Her career skyrocketed from there and resulted in her releasing six hit singles in a short time span.
Dee Messina was the first female country singer to have three number-one singles the lasted in that spot for multiple weeks. Her albums were very successful and received one gold and two platinum certificates from the RIAA. The Massachusetts-born singer sold over five million copies worldwide and managed to become a multi-millionaire in the process with a net worth of almost $10 million. She has released six albums to date and her most successful singles are "Bye, Bye," "I'm Alright," "Stand Beside Me," "Bring on the Rain," and "My Give a Damn's Busted".
The Dixie Chicks
Net Worth: $40 million
Venture: Someday
This trio of country singers is the fantasy of every country music lover out there. Together, Martie Maguire, Emily Erwin, and Natalie Maines have more combined musical talent and beauty points than we know what to do with. After almost two decades of the trio’s relatively quiet and eager waiting from fans, the Dixie Chicks are finally working on their fourth studio album, Someday, which will undoubtedly be a bestseller.
The three singers first started touring together in Dallas and have found popularity with the country crowded with their unique set of voices and talents. Despite their short time together and very long hiatus, the trio’s best hit singles “There’s Your Trouble,” and “Wide Open Spaces” helped them received three Grammy awards over the years and sell millions of albums over the years. The moral of the lesson is, if you’re going to take a two-decades-long hiatus, make sure you do it after creating a raving fan base that’s going to keep consuming your material and eagerly waiting for your return.
Jerry Jeff Walker
Net Worth: $200,000
Venture: Mr. Bojangles
With over 5 decades of experience in the music industry, you can definitely say that Jerry Jeff Walker has been around the block. In fact, he has been circled the block many, many times and still keeps going. Jeff Walker, also known as Gypsy Songman, is a country and outlaw-country singer that comes from a family of musicians that goes back to his grandparents. He is currently 77 years old and still tours around the US.
Jeff Walker has been producing music consistently over the past 5 decades, with 38 albums attributed to his name. His best known single to date is the song “Mr. Bojangles.” The song has since been recorded by many other artists including the Nitty Gritty Dirt Band in 1970. Walker claims he was inspired to write the song while serving time in jail for public intoxication. He met a man who referred to himself as "Mr. Bojangles" which was the source for the single’s title.