Pop Stars Who Tried And Failed To Go Country

Once upon a time, rock and country went together about as well as oil and water, cats and dogs, or Montagues and Capulets. One of the most famous moments in country music history is when in 1975 Charlie Rich, after announcing the CMA award for Best Entertainer had gone to John Denver, lit the nomination envelope on fire in protest. But things have changed in the decades since then, and crossover recordings are becoming more accepted. When once country stars “broke out” into rock, now the rock stars are going the other way, mainly because country music fans still buy music and their demographic is older, so the market is much more stable. Here are the most surprising country wannabe artists and how well they were received:

Justin Timberlake

Mr. “Bringing Sexy Back” teamed up with country star Chris Stapleton at the 2015 Country Music Awards (aka CMAs) for a duet of “Tennessee Whiskey.” While the song and performance were well received he didn’t follow it up with more offerings, despite the persistent rumors of Timberlake crossing over. Whether or not he’ll do a solo country single is anyone’s guess.

Lady Gaga

In 2011, Lady Gaga surprised a lot of people, tweaking the lyrics to “Born This Way” to fit a more country music style in what is known as “Born This Way (The Country Road Version).” Unfortunately, the country music press was less than impressed, with a CMT reporter stating, “I doubt a song that even hints at things like drag queens would ever make it on country radio.”


Amid the acclaim for Beyoncé’s masterwork “Lemonade,” surprisingly little has been said about the one track no one expected to hear: a deliberate, definite country track called “Daddy Lessons,” which showcases her Texas roots. Unfortunately the song got much higher on international charts than the U.S. ones, but a remix version with the Dixie Chicks has proved popular, so, perhaps this won’t be the last of Country Bey.


No one could predict where her career would go after her long, drawn out legal battle against producer Dr. Luke, but no one foresaw the pop star to slide into country territory with her album “Rainbow,” featuring such tracks as “Old Flame” and “Spaceship.” While these offerings didn’t do well on country charts, her fans weren’t just pleasantly surprised, they were ecstatic at the range she displayed and “Ke$ha made me like country music” became a viral meme.

Jessica Simpson

After wrecking a Dolly Parton tune during the Kennedy Center Honors broadcast in 2006, no one could have foreseen Jessica would make a second country attempt with a full album two years later. The album “Do You Know” actually debuted at number one on the charts, but it did not stay there long as word of mouth trashed the work as being too slickly produced and inauthentic. Plans for a second country album were abandoned shortly thereafter, and the country experiment ended.

Bret Michaels

Bret Michaels was the lead singer in Poison, an iconic 80’s hair band that did not make it to the 21st century. Michaels, after a mid life skid that included car crashes and reality television, released a country album called “Freedom of Sound.” Critics and fans laughed at his lyrics and the album, and the only song to hit the charts was a duet number with country songstress Jessica Andrews—and even then it failed to make the Top 40. Michaels blamed the insular country industry for his failure to launch.

Christina Aguilera

In 2012, Christina Aguilera recorded a country duet with Blake Shelton, her fellow judge on “The Voice,” hoping to capitalize on the show’s success. The pair performed the song, “Just a Fool,” on the show. The song peaked at No. 71 on the Billboard Hot 100, but failed to make the country charts, perhaps unsurprisingly. Slant Magazine called the song “an out-of-place country-pop duet” and the collaboration with Blake Shelton “a cheap cash-in.”

Steven Tyler

Aerosmith’s frontman Steven Tyler decided to go solo in country country in 2013. The album “We’re All Somebody from Somewhere” released in 2016 but it was his 2015 breakout hit “Love Is Your Name” that established his bona fides. It will take a lot more for Tyler to get up to Aerosmith-level popularity on the country charts, though; his album was dismissed in some circles as, ironically enough, “too mainstream.”

John Mayer

Prolific acoustic artist John Meyer took a detour into the countryside with his 2017 release “In The Blood,” his first and so far only song to make the Billboard Country chart. Whether it was a one-off or just the first of many has yet to be seen.

LL Cool J

Brad Paisley has been a country staple for years, but in 2013 he made an ill-advised attempt at solving racism by teaming up with rap star LL Cool J for a song that to this day is eye-rollingly inadequate to the task. The song was called “Accidental Racist.” Fans of both stars hated the project, critics panned it, and the sales were abysmal. For something that was supposed to help “the conversation about racism” it did nothing but start a conversation on what not to do on a record.