Cassadee Pope
Net Worth: $4 million
Venture: Stages
Former lead singer of the popular country band Hey Monday, Cassadee Pope, has managed to build herself an impressive fan audience in just a few years after going her own way once the band reached its end (formally a hiatus) in 2011. Pope has released two albums and three EPs while being the singer of Hey Monday and has so far released a self-titled EP in 2012. They were followed by Frame by Frame, a number-one in the country charts, and Stages which came out just this year for digital download, although it had a much weaker reception. Our favorite singles from the talented country singer are, “Wasting All These Tears” which came out in 2013 and reached over a million sales (earning it a Platinum status by the RIAA), and “Think of You”, a single featuring Chris Young which sold over 500,000 copies and also achieved Platinum status.
Pope has achieved many awesome victories in her short solo career, including being the first female winner of The Voice, being awarded the Breakthrough Video of the Year by CMT for hit single, “Wasting All These Tears”, and was nominated for a Grammy award for Best Country Duo/Group Performance due to the aforementioned “Think of You” duet with Chris Young. She was also chosen as the Top Indie Artist of 2018 by the Taste of Country Fan Choice Awards.
Alan Jackson
Net Worth: $75 million
Venture: Nashville
With over 80 million albums sold and 16 albums in his discography, old-school Country legend Alan Jackson’s is still going strong and keeps getting more and more interesting as time goes on. The top-selling singer and songwriter wrote almost all of his songs so far and is also engaged in other business ventures, such as a passion project with his daughter called Nashville.
Alan Jackson is highly respected and acclaimed in the Country scene. He has amassed a small fortune of over 75 million dollars over the years and has even been involved with Cracker Barrel and the Ford Motor Company. Jackson is also a very religious person, with two of his albums being dedicated to gospel music and two other albums centered around Christmas themes.
Jake Owen
Net Worth: $10 million
Venture: Thunder by the Bay
If you’re not yet familiar with pretty boy Jake Owen, you might be missing out on one awesome country singer. The singer debuted in 2006 with the album ‘Startin’ with Me’ which was fairly successful and resulted in three singles that reached the Top 20 on the charts. He followed it up with his second album, “Easy Does It” which also received favorable acclaim. It’s often true that the ‘third time’s the charm’, which is exactly what happened in Owen’s case. His third album, “Barefoot Blue Jean Night” outperformed the first two by a margin and got him the number-one country hit and the Top New Male Vocalist award from ACM.
Owen is an excellent golfer and occasionally plays pro golf. In June 2019, Jake was the subject of a small backlash from fans after covering Cher's song Believe to celebrate Gay Pride Month. He was promptly threatened with boycotts from many fans but chose to instead offer them a hug if they ever come to his concert, emphasizing that they "need one". The event has caused the musical artist to receive positive media coverage and a spike in his social media traffic..
Rascal Flatts
Net Worth: $150 million
Venture: Red Street Records
Originally formed in Columbus, Ohio, the Rascal Flatts are a popular musical group that combines popular music genres to create a delicacy of musical flavor called “country-rock-pop”. The band’s members include singer-songwriter Gary LeVox, Jay DeMarcus and Joe Rooney who are known to be second cousins. With seven best-selling albums to date, the group managed to secure an RIAA-certified platinum and diamond status for all their albums.
The group was first signed with Big Machine Records and went on to sign with Disney’s Lyric Street Records label. They have managed to build a very impressive net worth of $150 million and have succeeded in getting fourteen songs to the number-one spot in the charts since debuting. The band's longest-lasting number-one single is a 2005 cover of Marcus Hummon's "Bless the Broken Road", which spent five weeks in that position.
T.G. Sheppard
Net Worth: $1 million (estimated)
Venture: NASCAR T.G.
Shepard is known as a country music legend and is active to this day even as he pushes age 76. The singer was born in Tennessee and decided to drop out of high school at an early age and pursue a career in music. He began his musical career with the name of William Browder and quickly gained an audience with his single "Devil in the Bottle" which reached the number one hit on Billboard's Hot Country Singles Chart. From there the singer went on to produce numerous number-one hits in the US charts and even had eight consecutive number one hits in the early '80s.
G. Sheppard has since receded into a more modest life outside of the spotlight. His latest hit album was "One for the Money" and from there he would release an album ever 3-5 years with modest success. When asked about his stage name "T. G. Sheppard", he explains that as an executive at RCA, Browder didn't want to jeopardize his position by recording materials through other labels. He claims the stage name's initials (T. G.) are just random initials and don't really mean anything.