Net Worth: $14 million
Venture: The Estate of Harold Jenkins
Harold Lloyd Jenkins, mostly known as Conway Twitty, was a country singer from the ’60s and ’70s that dabbled in various genres from rock and roll to R&B and even Pop. He was widely praised for his duets with Loretta Lynn and was inducted into the Country Music Hall of Fame and the Rockabilly Hall of Fame following his passing away in 1993. His most successful songs include “Hello Darlin’,” “Honky Tonk Angel,” “Linda on My Mind” and “The High Priest of Country Music.”
Twitty was the center of various legal issues throughout his life, including alleged tax evasion and fights over his estate, including copyrights and royalties. The peak of his career was during the late ’70s when he shifted his musical style to country pop and changed his look from the slicked-back pompadour style to the regular curly hair and mustache.
Shania Twain
Net Worth: $400 million
Venture: Let’s Go!
With a net worth of over $400 million, Shania Twain is arguably the most successful female country singer in the world. With over 100 million album sales, she has pretty much smashed the glass ceiling for women in this musical genre and even went a few steps further.
Twain was born in Canada and became a famous artist after being discovered by producer Mutt Lange, whom she ended up marrying by the way. She is currently signed as a musician with Mercury-Nashville and is part of a sponsorship project named “Let’s Go!” that aims to help young artists find their voice and crowd.
Blake Shelton
Net Worth: $60 million
Venture: Ryman Hospitality
Singer, real estate investor, and Gwen Stefani's hubby, Blake Shelton is every girl’s dream — he’s got the looks, the money, and the voice to capture anyone’s attention. His debut single "Austin” was a massive success and landed him square inside the much-desired platinum status for the album’s sales.
Outside of music, the singer invests his multi-million dollar wealth into various industries and especially focuses on Ryman Hospitality, a hotel, resort, entertainment, and media company that owns a variety of real estate properties under its name.
Dolly Parton
Net Worth: $500 million
Venture: The Dollywood Company
The undisputed queen of country music, Dolly Parton, inspired millions of young men and women to freely express themselves and be their best versions through her many memorable and wildly popular songs. The legendary singer expertly used her immense income to found The Dollywood Company, which owns a water park, a dinner theater, and a spa resort.
Her musical and business achievements helped her secure a net worth of around half a billion-dollar, much of it thanks to her Dollywood theme park, which is the twenty-fourth most popular theme park in the United States.
Crystal Gayle
Net Worth: $10 million Venture: Crystal’s Fine Gifts and Jewelry
Crystal Gayle is a country singer, widely known as the sister of Loretta Lynn, and her famous single "Don't It Make My Brown Eyes Blue" topped the country charts and became an international success.
Gayle was the recipient of a Grammy Award and five Academy of Country Music awards. She was recently ranked by Rolling Stones as one of the greatest country artists of all time and received a star on the Hollywood Walk of Fame. She has released numerous albums that received Silver, Gold, and Platinum certifications. Despite fading in popularity after the '80s, Gayle has continued to tour and release albums over the years. Her latest album "You Don't Know Me: Classic Country" was released just a few months ago.