Modern Country Music
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50 free Modern Country Music trivia questions with answers — music quiz, new questions added Oct 2026.
Country music in the twenty-first century has been anything but settled. Rappers have topped its charts, pop stars have borrowed its banjos, and a wave of streaming-era singers now fills stadiums that once hosted only rock bands. Along the way the genre has argued, loudly, about who gets played on its radio stations. This modern country music trivia quiz runs from the 2000s to the 2020s: the talent-show discoveries, the viral breakouts, the duets and crossover smashes, the award-show moments and the Nashville rooms where careers began. Taylor Swift's early years, Carrie Underwood's rise, Zach Bryan and Kacey Musgraves all feature, alongside a few controversies that changed the business. It is written for fans who know today's hits by heart and for casual listeners who mostly hear them at weddings and tailgates. Each answer comes with a short explanation, so even the misses leave you with a story to tell.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which rapper's Old Town Road was pulled from Billboard's Hot Country Songs chart in 2019, igniting a row over genre?
Lil Nas X
Lil Nas X had climbed to number 19 on the country chart when the magazine ruled the song did not fit the genre. A remix with Billy Ray Cyrus followed that April.
Q 02Which country star's name did Taylor Swift use as the title of her debut single in 2006?
Tim McGraw
Tim McGraw came to Swift as an idea during a high school math class, and she finished writing it within 15 minutes. It was the first release from her debut album.
Q 03In which retail chain was 11-year-old Mason Ramsey filmed yodeling a Hank Williams song in 2018, earning a record deal?
Walmart
Walmart in Harrisburg, Illinois, was the setting for his clip of Lovesick Blues. Within weeks the viral video had won Ramsey a deal with Big Loud and Atlantic.
Q 04Which singer's 2023 cover of Fast Car made Tracy Chapman the first Black songwriter to win CMA Song of the Year?
Luke Combs
Luke Combs took his faithful cover to number one on country radio in July 2023. It won Chapman the Song of the Year prize 35 years after she released the original.
Q 05Which trio covered Tom Cochrane's Life Is a Highway for the soundtrack of Pixar's 2006 film Cars?
Rascal Flatts
Rascal Flatts cut the cover for the film, and it proved popular enough to be added as a bonus track to later copies of the group's album Me and My Gang.
Q 06Which restaurant chain revived its Oreo shake after Walker Hayes name-checked it in the 2021 hit Fancy Like?
Applebee's
Applebee's had dropped its Oreo Cookie Shake in the wake of the pandemic. The chain brought the dessert back once the song became a hit.
Q 07Which pop superstar became the first Black woman to top Billboard's Hot Country Songs chart, with Texas Hold 'Em?
Beyoncé
Beyoncé entered the chart at number one with the banjo-led single, a surprise release during the Super Bowl in February 2024. It appears on her album Cowboy Carter.
Q 08Which Taylor Swift video had just won at the 2009 MTV Video Music Awards when Kanye West interrupted her speech?
You Belong with Me
You Belong with Me had taken Best Female Video when West walked on and grabbed the microphone. Public opinion turned on him, and President Obama called him a jackass.
Q 09Which weekly NFL broadcast began opening with a Carrie Underwood theme song in 2013, when she took over from Faith Hill?
Sunday Night Football
Sunday Night Football has changed Underwood's theme more than once. In 2018 she co-wrote a brand-new opener for the show called Game On.
Q 10Which artist's 2024 hit A Bar Song (Tipsy) reworks a 2004 J-Kwon rap single and spent 19 weeks atop the Hot 100?
Shaboozey
Shaboozey became the first Black man to sit at number one on the Hot 100 and Hot Country Songs at the same time. His 19 weeks tied the all-time record of the day.
Q 11Which singer from Sneedville, Tennessee, competed on The Voice in 2014 and later released the album One Thing at a Time?
Morgan Wallen
Morgan Wallen had hoped to play college baseball as a pitcher and shortstop until he tore an elbow ligament in his senior year. The 2023 album spent 19 weeks at number one.
Q 12Which former SteelDrivers frontman sang Tennessee Whiskey with Justin Timberlake at the 2015 CMA Awards?
Chris Stapleton
Chris Stapleton won three trophies that night, including New Artist of the Year. He had already co-written number-one hits for George Strait and Josh Turner.
Q 13Which Kacey Musgraves album, partly recorded above Sheryl Crow's horse stable, won the Album of the Year Grammy in 2019?
Golden Hour
Q 21Which TV talent show did Carrie Underwood win in 2005 before returning to it as a judge two decades later?
American Idol
American Idol made Underwood its fourth champion, and Forbes later declared her the most successful winner the show has produced. She joined its judging panel in 2025.
Q 22Which New Zealand-born guitarist, raised in Australia, married actress Nicole Kidman in Sydney in 2006?
Keith Urban
Keith Urban met Kidman at a Hollywood event promoting Australia in 2005. He was the first New Zealand-born man to reach the top 10 of the US country charts.
Q 23Which singer from Lindale, Texas, finished third on Nashville Star in 2003 and later formed the trio Pistol Annies?
Miranda Lambert
Golden Hour won all four Grammys it was nominated for that night. Musgraves has said she wrote two of its songs under the influence of LSD.
Q 14Which Zach Bryan duet with Kacey Musgraves entered the Hot 100 at number one in 2023, a first for both singers?
I Remember Everything
I Remember Everything was the first song to top the Hot 100, Hot Country Songs and Hot Rock & Alternative Songs charts all at once. It later won the pair a Grammy.
Q 15Which Louisiana singer made her acting debut as Abby on Yellowstone and won CMA Entertainer of the Year in 2023?
Lainey Wilson
Lainey Wilson was the first woman to take that prize since Taylor Swift in 2011. On first moving to Nashville she lived in a camper trailer outside a recording studio.
Q 16Which Nashville rapper turned country singer scored his first country radio number one with Son of a Sinner in 2023?
Jelly Roll
Jelly Roll got the nickname from his mother, for his childhood fondness for doughnuts. He spent years in and out of jail before his music took off.
Q 17Which rapper-singer's 2024 country album F-1 Trillion features guests including Dolly Parton and Hank Williams Jr.?
Post Malone
Post Malone first reached the country chart in 2023, singing on a re-recording of Joe Diffie's Pickup Man. A year later he had a whole album of Nashville duets.
Q 18Which rapper joined Florida Georgia Line on a 2013 remix of Cruise that carried the country hit into the pop top 10?
Nelly
Nelly helped Cruise become the best-selling digital country song of its day, with over 7 million copies sold. It also spent a then-record 24 weeks atop Hot Country Songs.
Q 19Which pair of singers who met at a Nashville house party in 2012 went on to score hits with Tequila and Speechless?
Dan + Shay
Dan + Shay started writing together the day after they met. The duo later won the Grammy for Best Country Duo/Group Performance three years running.
Q 20Which Oklahoma-born singer of the 2001 hit Austin was an original coach on NBC's The Voice, staying until 2023?
Blake Shelton
Blake Shelton coached the winning singer in nine of his 23 seasons on the show. In 2017 he became the first country artist named People's Sexiest Man Alive.
Miranda Lambert caught the attention of a Sony executive who was judging the show and who persuaded the label to sign her. She unveiled Pistol Annies in 2011.
Q 24Which Hootie & the Blowfish frontman went country and took a cover of Wagon Wheel to number one in 2013?
Darius Rucker
Darius Rucker became the first Black artist to win the CMA's New Artist award, in 2009. The song he covered was written by Bob Dylan and Ketch Secor of Old Crow Medicine Show.
Q 25Which singer won fans sharing covers on Facebook, then topped all five main Billboard country charts at once in 2017?
Kane Brown
Kane Brown was the first artist to manage that sweep. It was powered by What Ifs, a duet with Lauren Alaina, and the new song Heaven.
Q 26Which singer in trademark aviators was fired as a tour opener for overrunning his set, then replaced by Taylor Swift?
Eric Church
Eric Church told Swift she should thank him with her first gold record, and she later sent it. Her note thanked him for playing too long and too loud.
Q 27Which Macon-born singer's 2011 hit Dirt Road Anthem, with its rapped verses, was first recorded by co-writer Colt Ford?
Jason Aldean
Jason Aldean said he did not consider the track a rap song. That did not stop Ludacris from adding a hip-hop verse for a remix after the two performed it at the CMT Music Awards.
Q 28Which West Virginia guitarist won CMA Entertainer of the Year in 2010 on a night he co-hosted with Carrie Underwood?
Brad Paisley
Brad Paisley got his first guitar, a Sears Silvertone, from his grandfather at age eight. He and Underwood fronted the awards show together from 2008 to 2018.
Q 29Which Tennessee stadium headliner named his fan club No Shoes Nation at a 2012 concert in Foxborough?
Kenny Chesney
Kenny Chesney took the name from his hit No Shoes, No Shirt, No Problem. The fan club flies a black flag with a white skull and crossbones.
Q 30Which duo of Jennifer Nettles and Kristian Bush began as a trio in Atlanta's folk-rock scene before hits like Stay?
Sugarland
Sugarland lost founding member Kristen Hall at the end of 2005, when she left to stay home and write songs. The remaining pair kept the name and carried on as two.