There’s nothing better than having someone to share your success with once you’ve made it to the top, and this is no different in the case of your favorite country music stars. Some of them have long-standing love stories while some have had their fair share of heartbreaks.

At the end of the day, the most important thing is having the support of someone through your triumphs and losses, as the feeling of being accompanied by someone you love through this journey called life is worth more than gold. Let’s see some of the richest stars of country music and their relationships with their significant others.

Shania Twain (53) Estimated $400 Million

Canadian singer-songwriter and actress Shania Twain is the best-selling female singer in the history of country music. She rose to fame in 1995 with her album The Woman In Me, which was produced by Robert Lange who eventually became her first husband.

Twain and Lange divorced after 14 years of marriage after allegations of infidelity on Lange’s part with Shania’s best friend, Marie-Anne Thiébaud. Twain, ironically enough, gave love a second chance and married Marie-Anne’s ex-husband, Frederic Thiébaud. Shania finished her most recent tour called the Now Tour in December 2018.

Taylor Swift (29) Estimated $360 Million

Taylor Swift, the American singer-songwriter who is famous for writing songs about her past relationships, seems to be over the moon with her current romance. Pictures of the Love Story singer while enjoying coffee with actor Joe Alwyn in Nashville made celebrity news. The two have reportedly been dating since 2017.

Swift, who’s just released a new song titled Me! with Panic! At the Disco’s Brendon Urie in 2019, has done a fantastic job in keeping their relationship under wraps. In fact, they have yet to make a red carpet appearance together. Maybe this will be a keeper!

Toby Keith (57) Estimated $365 Million

Toby Keith is a country singer-songwriter, producer, and actor. He has released over 19 studio albums, five compilation albums, and two Christmas albums. The Should’ve Been a Cowboy singer has sold over 40 million albums with annual earnings estimated to be around $53 Million.

Toby married his wife, Tricia Lucus, in 1986 when they were both in their 20s. The couple has three children; two daughters and a son. Keith’s latest tour Should’ve Been A Cowboy XXV, which was named after his first single and country hit, concluded in October 2018.

Garth Brooks (57) Estimated $330 Million

Singer Garth Brooks is one of the world’s best-selling artists of all time with over 170 million albums sold. The Thunder Rolls singer became known in country music for his integration of elements of rock, which set him apart from the rest of the singers of the genre.

Garth married his high school sweetheart and had three daughters, but they got a divorce after 15 years of marriage. He then got married for the second time to country singer Trisha Yearwood. Garth currently has an upcoming studio album in 2019 called Fun.

Kenny Chesney (51) Estimated $190 Million

Kenny Chesney is one of the most important country singers in the US. He’s also a songwriter and record producer and has had 14 certified gold albums throughout his career. His most recent album, Songs for the Saints, was released in 2018.

Kenny’s love life made headlines when he married actress Renee Zellweger only four months after they met each other. The relationship didn’t work out, and they ended up getting an annulment. He was then said to be dating the actress and pageant queen Jamie Hill, but it turned out to be only rumors. Reports say that Chesney is in a long-term relationship with Mary Nolan.

Kris Kristofferson (82) Estimated $160 Million

American singer, songwriter, and actor Kris Kristofferson is known for being a member of the group who pioneered the outlaw country subgenre, The Highwaymen. Kris has also found success in acting and even won a Golden Globe for Best Actor for his performance in the 1976 movie, A Star is Born.

Kris was said to have dated many girls (including famous ones) back in the day—from Janis Joplin to Barbra Streisand. But he ended up marrying makeup artist Lisa Meyer in 1983. Five kids later and their marriage still going strong after all those years. His most recent album, 2016’s The Cedar Creek Sessions, earned him a Grammy nomination for Best Americana Album.

Linda Ronstadt (72) Estimated $130 Million

Linda Ronstadt is a retired American singer famous for dabbling into many music genres throughout her career. She’s a 10-time Grammy Award-winning artist, and, this year, she is set to receive a star in the Hollywood Walk Of Fame with Dolly Parton and Emmylou Harris for their work as the Trio.

Linda never married, but she dated some men in her youth—most notably former California governor Jerry Brown. Ronstadt didn’t mind being single as she was able to become a mother through adoption when she welcomed two children into her life. Lisa revealed in 2013 that she has Parkinson’s disease, which is the reason she is unable to perform anymore.

Brad Paisley (46) Estimated $95 Million

Brad Paisley is one of the most successful American country singers in the music industry today. He has released eleven studio albums, which are all certified gold or higher and has sold more than 11 million copies. So, him having a fat bank account is to be expected.

The She’s Everything singer has been married to TV actress Kimberly Williams since 2003. The couple lives in Tennessee and shares two sons together, 12-year-old William and 10-year-old Jasper. Brad and Kimberly partnered with Belmont University to open a free referral-based year-round grocery store called The Store to help out their community.

Alan Jackson (60) Estimated $95 Million

American singer and songwriter Alan Jackson is noted for being one of the artists who have honored the traditional style of country music with his songs. The Remember When singer is also part of the Georgia Music Hall of Fame and the Country Music Hall of Fame.

Jackson tied the knot with his high school sweetheart, Denise, with whom he has three daughters. They separated for a while under infidelity allegations but eventually got together again. Denise has written two books, with one being about the relationship. Alan’s most recent song is The Older I Get, which was released in 2017.

Reba McEntire (64) Estimated $95 Million

Reba McEntire is an American singer, songwriter, record producer, and actress famous in the country music scene. Reba, who was dubbed the Queen of Country at one point, also branched out into acting. She’s appeared in films, Broadway productions, and her own sitcom.

Reba has been married twice, first to Charlie Battles and then to her manager and former guitar player Narvel Blackstock (shown in the photo above). However, the couple filed for divorce in 2015 after 26 years together. Reba is currently dating a photographer named Anthony Lasuzzo whom she’s totally in love with, as she revealed in an interview.

Luke Bryan (42) Estimated $120 Million

American singer Luke Bryan has had a formidable career in country music.  He’s sold over 7 million records and over 27 million singles worldwide. He released his latest album, What Makes You Country, in 2016 and has recently returned as a judge in the 17th season of American Idol.

Bryan met his wife Caroline Boyer while attending the Georgia Southern University. Luke was a senior then while Caroline was a freshman. The two have been married since 2006 and have two children together—Thomas and Tatum who are 11 and 9 years old respectively.

Carrie Underwood (36) Estimated $85 Million

Carrie Underwood has been one of the most popular country singers of our generation. But Carrie wasn’t just blessed with amazing pipes, she’s also a songwriter and actress. She rose to fame after becoming the winner of the 4th season of American Idol.

Carrie has since become one of the best-selling artists in country music history. Underwood has been with her husband, NFL player Mike Fisher, since 2008. The couple announced their engagement in 2009 and they married the next year. She just gave birth to their baby no. 2 in January 2019.

Tim McGraw (52) Estimated $85 Million

American singer Tim McGraw is one of the biggest names in the country music scene today with numerous top-charter albums and singles under his belt. Recently, he released two singles titled Neon Church and Thought About You. Tim also has a pilot license and owns a jet, which he flies often as his favorite pastime.

McGraw married fellow country singer Faith Hill in 1996. The couple met backstage at a Country Radio Seminar and have recorded many duets together. They have three daughters and have one of the most solid relationships in Hollywood.

Jason Aldean (42) Estimated $80 Million

Jason Aldean is a country singer who has had a countless number of hits gracing the charts, including songs such as Big Green Tractor, Drowns the Whiskey, and She’s Country. Almost every one of his albums is certified platinum and 2010’s My Kinda Party was certified quadruple-platinum.

The You Make It Easy singer married the former American Idol contestant Brittany Kerr in 2015 after his divorce from first wife, Jessica Ann Ussery. The couple has two children and recently welcomed their youngest one in February 2019. Aldean’s most recent album was released in 2018 and it’s called Rearview Town.

Faith Hill (51) Estimated $80 Million

Audrey Faith Hill McGraw, whose professional name is Faith Hill, is one of the most successful country singers of all times. She’s a money machine who has sold more than 40 million albums worldwide. Some of her most popular hits include This Kiss, There You’ll Be, and It Matters to Me.

Faith is married to country star Tim McGraw, and the two of them have recorded a number of duets together over the years. They have one of the most solid marriages in the business and share three daughters—Gracie, Maggie, and Audrey. Faith’s most recent album was a collaboration with her husband, Tim, in 2017 called The Rest Of Our Lives.  

Keith Urban (51) Estimated $75 Million

New Zealand-Australian singer, songwriter, and record producer Keith Urban rose to fame in 1991 after releasing his debut album in his home country. He then moved to the United States and has since found immense success in the music industry. Keith’s most recent album, Graffiti U, was released in 2018. It has the singles Female (inspired by the MeToo movement), Parallel Line, and Coming Home.

The Somebody Like You singer is married to Australian Hollywood actress Nicole Kidman. Despite being constant names in celebrity news when they started dating, they proved to be the real deal. They have been together since 2006 and have two daughters together. 

George Strait (67) Estimated $300 Million

George Strait, also known as the King of Country, recently released a new album called Honky Tonk Time Machine in March 2019. Strait has been married to his lady love, Norma Strait, for quite some time now—48 years to be exact. The couple met in high school as they were both from the same little town.

George revealed in an interview that he asked her on a date once, but they didn’t see each other for a while until he realized she was the love of his life. They then resumed their romance, and the I Cross My Heart singer decided to put a ring on it in 1971.

 

Loretta Lynn (87) Estimated $65 Million

Loretta Lynn is one of the country music singers and songwriters with the longest careers, having been in the industry for almost 60 years. She’s considered to have done groundbreaking work in the industry and is the most awarded female singer in the history of country music.

With such a long career, Loretta has amassed a big fortune with a staggering net worth of $65 million—more than enough for her retirement! But the 87-year-old Loretta keeps on working and even released her album, Wouldn’t It Be Great, in 2018. She was married to her husband Oliver Vanetta Lynn Jr. until his death in 1996.

Tanya Tucker (60) Estimated $60 Million

American country singer Tanya Tucker had her first hit at the tender age of 13. Fortunately for her, her audience grew up with her and she stayed relevant and popular while growing into adulthood. She’s had a number of hits throughout her career including songs such as What’s Your Mama’s Name? and Blood Red and Goin’ Down.

Tanya was part of the Outlaw Country movement and was involved romantically with several artists in the ‘80s. But she’s had an intermittent relationship with Jerry Laseter since they announced their engagement in 1997. They eventually called off their wedding but didn’t split officially. Tanya’s upcoming album, While I’m Livin‘, will be released in 2019.

Gary LeVox (48) Estimated $50 Million

American singer Gary LeVox is a country star known for being the lead vocalist of the country-pop trio Rascal Flatts. LeVox, whose real name is Gary Wayne Vernon Jr., took his stage name from a studio console. LeVox and his group released their latest album Back To Us in 2017.

The Life is a Highway singer has said that his relationship with wife, Tara Vernon, is the kind of love story you read in books as it was love at first sight after they met backstage in a festival concert. The couple has two daughters together.

Joe Don Rooney (43) Estimated $50 Million

American musician and lead guitarist of the country-pop trio Rascal Flatts Joe Don Rooney, who’s also known as J.D Rooney, is famous for playing a myriad of musical instruments in the band. Besides playing the electric guitar, Rooney also plays the acoustic guitar, bass, mandolin, and banjo.

Rooney has been married to beauty queen and model Tiffany Fallon. She was crowned as Miss Georgia in 2001 and placed 2nd runner-up for Miss USA that same year. The couple married in 2006 and lives together in Tennessee with their three children.

Jay DeMarcus (48)  Estimated $50 Million

Jay DeMarcus is an American musician, bassist, pianist, songwriter, and record producer. Jay is one-third of the country-pop trio, Rascal Flatts, but he’s also a renowned record producer in Nashville. Aside from making music, Jay and his band have also made some appearances on the small screen in shows like CSI, Nashville, and Drop Dead Diva.

DeMarcus has been married to his beauty queen wife, Allison Alderson, since 2004. They have children, but DeMarcus also had a daughter from a previous relationship who was put up for adoption since the mother didn’t want to raise the child.

Randy Owen (69) Estimated $50 Million

Randy Owen is a famous American country music artist famous for being the lead singer in the country rock group Alabama. The band had immense success during the ‘80s, with 27 hit singles. Thus, becoming the most successful band in country history.

They have released more than 20 gold albums. Although the band dissolved in 2003, they reunited again in 2010 and continued to tour. Their latest album, Southern Drawl, was released in 2015. Owen has been married to wife Kelly Owen since 1975, and they have three children together.

Miranda Lambert (35) Estimated $45 Million

Miranda Lambert is an American country superstar, Grammy winner, and songwriter. She also rose to fame after competing in a TV contest show called Nashville Star and subsequently releasing her debut album. Since then, she has become one of the most important female singers in the genre.

Miranda has been involved romantically with several musicians. She married Blake Shelton in 2011, but they filed for divorce after four years. She then briefly dated Anderson Eaton (depicted in the picture) before revealing she had married NYPD officer Brendan McLoughlin. Miranda’s recently announced she was ready to come out from her break from the spotlight and will be releasing new music soon.

Dwight Yoakam (62) Estimated $45 Million

Singer, songwriter, and actor Dwight Yoakam is known for having a very unique country music style. He’s had massive success in the charts and in sales, with more than 25 million albums sold in his career. Last year, Dwight embarked on his LSD tour alongside Steve Earle and Lucinda Williams.

Despite being linked to several famous singers and actresses, Yoakam has never been married. He has been dating photographer Emily Joyce since 2013, and they are rumored to be engaged. However, the truth is they haven’t made any announcement of their engagement publicly.

Kix Brooks (64) Estimated $45 Million

American country singer Kix Brooks is also a film producer and actor most known for being part of the Brooks & Dunn duo. He’s also famous for hosting radio’s American Country Countdown. Kix’s career after the duo has also been successful, with his latest single, There’s The Sun, peaking at 48 on the charts.

Kix also appeared in the 2018 Hallmark movie Home By Spring. Brooks has been married to his wife, Barbara Brooks (who is an accomplished horse cutter), since 1981. They celebrated their wedding in the city of Nashville. They are now parents to two children.

Ronnie Dunn (66) Estimated $45 Million

Ronnie Dunn is a known country singer, record executive, and songwriter. He’s the other half of the Brooks & Dunn duo. Dunn has also had a good career after going solo in 2011. He released his third solo album, Tattooed Heart, in 2016.

Dunn married his amazing wife, Janine, in 1990. She’s supported him in all of his projects ever since and they have raised three children together. The couple lives a quiet and peaceful life amid nature in a farm they call “The Barn”. It is a 600-acre property right outside of Nashville, Tennessee.

Trisha Yearwood (54) Estimated $40 Million

Trisha Yearwood is one of those artists who can do it all. She’s a singer, songwriter, author, actress, chef, and TV host. She’s not only been successful in the music scene, but she’s also written several books, which made her a New York Times Best-selling author.

Trisha also has her own cooking show called Trisha’s Southern Kitchen, which has earned her a Daytime Emmy Award. The She’s In Love With the Boy singer has been married a few times, but she tied the knot with her current husband, singer Garth Brooks, in 2005 at their home in Owasso, Oklahoma.

Dierks Bentley (43) Estimated $30 Million

Singer Dierks Bentley is a country superstar who rose to fame after he released his self-titled album 16 years ago. He has several works in his discography which are certified gold and platinum, and his latest album, The Mountain, debuted in the #1 spot of the Top Country Albums chart.

The Burning Man singer has been married to his wife, Cassidy Black, for 14 years now. They live a happy tranquil life in Nashville with their family composed of their three children—Jordan Catherine, Evelyn Day, and Knox—and their two dogs.

Dolly Parton (73) Estimated $500 Million

You can’t talk about country music without mentioning the queen of the genre, Dolly Parton. She’s a singer-songwriter, businesswoman, author, producer, and actress who has had one of the most successful careers in the industry. She has the most impressive bank account out of everyone on this list, too!

Dolly has written over 3,000 songs, including the chart-topper I Will Always Love You and her arguably most famous tune, Jolene. Parton, who recently wrote the soundtrack for the 2018 Netflix movie, Dumplin’, has been with her husband, Carl Dean, since 1964. However, they keep their relationship very private and rarely get photographed together in public.

Kenny Rogers (80) Estimated $250 Million

Kenny Rogers is an American singer and record producer who is a member of the Country Music Hall of Fame. He’s also one of the best-selling artists of all time. Rogers also found success as an entrepreneur through the restaurant chain, Kenny Rogers Roasters. His love life, however, is a bit more complicated.

Kenny has been married five times. He married his current wife, Wanda Miller, after his fourth divorce in 1993. The couple has remained stable and has two children together. In 2015, Rogers announced his retirement tour, The Gambler’s Last Deal, which had shows until 2018. Unfortunately, he had to cancel his remaining tour dates in 2018 because of his health issues.

Zac Brown (40) Estimated $25 Million

The Zac Brown Band is an American country band led by Zachary Alexander “Zac” Brown and is composed of notable musicians such as John Driskell Hopkins, Clay Cook, Matt Mangano, Chris Fryar, Daniel De Los Reyes, and Coy Bowles. The band is currently on their The Owl Tour. 

Zac has been surrounded by drama involving leagal issues and substance abuse. He’s also sadly separating from his wife, jewelry designer Shelly, after 12 years, but at least it’s in an amicable way. The couple married back in 2006 and share five children.

Blake Shelton (42) Estimated $60 Million

Blake Shelton is a famous American country singer, but he’s also equally known for his career in television. He’s been the judge of the TV talent show The Voice since it’s first season in 2011. He’s also noted for having six wins out of the sixteen seasons under his belt.

Blake was married to fellow country singer Miranda Lambert until they announced their divorce in 2015. Shortly after, the God Gave Me You singer started a relationship with singer Gwen Stefani.  Blake released his 11th album, Texoma Shore, in 2017. It debuted at number 4 at the Billboard 200.