90s Country Music Trivia
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46 free 90s Country Music trivia questions with answers — music quiz, new questions added Oct 2026.
40 free 90s Country Music trivia questions with answers. The 1990s were the decade country music stopped being a regional format and started filling stadiums. These 46 questions cover how it happened: the Oklahoman who fused neotraditional country with arena rock, the album that opened at number one on the pop chart, the free concert that drew almost a million people to Central Park, and the alter ego nobody asked for. There are rounds on Shania Twain and the best-selling album ever made by a female solo artist, on the Dixie Chicks and their platinum certifications, on George Strait's record 60 number ones, on Alan Jackson's run of traditionalist hits, and on the line-dance single that started life under a completely different title. Every answer was checked against a primary reference before publication, so the sales figures, chart positions and dates here are accurate rather than approximate. Play it solo, or use it as a round for anyone who still owns the CDs.
30 of 46 questions with answers and explanations. Play the quiz
Q 01Which song, a country number one in 1993, was Toby Keith's debut single?
Should've Been a Cowboy
'Should've Been a Cowboy' nods to Gunsmoke's Marshal Dillon and Miss Kitty; Keith wrote it after seeing a cowgirl turn down an older man in his party, then take the floor with a young cowboy.
Q 02Which 1996 Deana Carter hit recalls a first love during a summer on her grandparents' farm?
Strawberry Wine
'Strawberry Wine' drew on co-writer Matraca Berg's own teenage summers on her grandparents' Wisconsin dairy farm; Carter's recording was the CMA's Single of the Year in 1997.
Q 03Where is that superstar from?
Oklahoma
Oklahoma is his home state: he was born in Tulsa on February 7, 1962, grew up in Yukon and studied advertising at Oklahoma State University in Stillwater before moving to Nashville.
Q 04Which 1991 Garth Brooks single had a video about domestic violence that TNN and CMT refused to air?
The Thunder Rolls
'The Thunder Rolls' was pulled by both networks over its domestic-violence storyline, yet the video went on to win the CMA's Video of the Year award that October.
Q 05Which 1990 Garth Brooks album, featuring 'Unanswered Prayers', became his best-selling studio album?
No Fences
No Fences, his second album, has shipped 18 million copies in the US; its 'Unanswered Prayers' retells Brooks, out with his wife Sandy, running into his old high-school flame.
Q 06Which 1991 Garth Brooks album was the first country album to enter the Billboard 200 at number one?
Ropin' the Wind
Ropin' the Wind arrived at number one in September 1991, knocking Metallica's self-titled album off the top, and spent 18 weeks there in all.
Q 07Which rock star, writer of the Garth Brooks hit 'Shameless', joined Brooks on stage in Central Park in 1997?
Billy Joel
Billy Joel walked on as a special guest and sang 'New York State of Mind' with Brooks at the free show on August 7, 1997; estimates of the crowd range from 250,000 to more than a million.
Q 08What was the name of the rock alter ego Garth Brooks adopted in 1999?
Chris Gaines
Chris Gaines was the brooding Australian rock star he played on the 1999 album In the Life of Chris Gaines, billed as a pre-soundtrack for a film, The Lamb, that was never made.
Q 09Why did Garth Brooks announce his retirement from recording and touring in October 2000?
To raise his daughters
To raise his daughters, Taylor, August and Allie, he stepped back after the 2001 album Scarecrow and said he would not tour again until the youngest had finished high school.
Q 10Shania Twain, born Eilleen Edwards, took her surname from whom?
Her stepfather
Her stepfather, Jerry Twain, an Ojibwa forestry worker, adopted Eilleen and her siblings when she was a small child and had their surname legally changed to his.
Q 11Which 1997 country album is the best-selling studio album ever released by a female solo artist?
Come On Over
Come On Over, by Shania Twain, has sold more than 40 million copies worldwide, helped by singles that crossed from country to pop radio, three of them reaching the top ten of the Hot 100.
Q 12Which rock producer phoned Shania Twain after hearing her debut, then co-wrote her hits and married her in 1993?
Mutt Lange
Mutt Lange, producer of AC/DC's Back in Black and Def Leppard's Hysteria, wrote with her by telephone for months before they met at Nashville's Fan Fair in June 1993; they married that December.
Q 13Which Shania Twain ballad won Best Country Song and Best Female Country Vocal Performance at the 1999 Grammys?
Q 21What did the Dixie Chicks do at the 2007 Grammy Awards?
Swept all five nominations
Swept all five nominations, including Album, Record and Song of the Year, four years after many country stations dropped them over their singer's criticism of President Bush.
Q 22Which Garth Brooks ballad's video shows figures who died chasing their dreams, including President Kennedy and Martin Luther King?
The Dance
'The Dance' was written by Tony Arata, who recalls that Brooks, still unsigned, heard it at a songwriters' night and swore to record it if he ever got a deal; it won the ACM's Song and Video of the Year awards.
Q 23Which Reba McEntire hit, a Bobbie Gentry cover, follows a poor girl sent out by her mother in a red dress?
You're Still the One
'You're Still the One' answered those who said her marriage would not last; it also reached number two on the Hot 100, her biggest pop hit.
Q 14Which Shania Twain video gender-flips Robert Palmer's 'Addicted to Love', with male models as her band?
Man! I Feel Like a Woman!
'Man! I Feel Like a Woman!' won her a second straight Grammy for Best Female Country Vocal Performance, and she opened her 2003 Super Bowl halftime set with it.
Q 15Which 1992 single by Billy Ray Cyrus set off a nationwide line dance craze?
Achy Breaky Heart
'Achy Breaky Heart', written by Don Von Tress, reached number one on the country chart in 1992, and its video, built around a choreographed dance, is credited with taking line dancing mainstream.
Q 16Which country duo bowed out with a 1991 farewell tour after Naomi, its elder half, was diagnosed with hepatitis C?
The Judds
The Judds, mother Naomi and daughter Wynonna, closed their Farewell Tour with a pay-per-view concert in December 1991; Wynonna launched her solo career the following year.
Q 17Which band's 1999 ballad 'Amazed' later became the first country hit to top the Hot 100 since 'Islands in the Stream'?
Lonestar
Lonestar spent eight weeks atop the country chart with 'Amazed' in 1999; a pop remix then carried it to number one on the Hot 100 in 2000.
Q 18How are Dixie Chicks founders Martie Maguire and Emily Strayer related?
Sisters
Sisters, born Martie and Emily Erwin, they founded the band in 1989 on fiddle and banjo, and later recorded as a duo under the name Court Yard Hounds.
Q 19Who became the Dixie Chicks' lead singer in 1995, shortly before they signed a major-label deal?
Natalie Maines
Natalie Maines was recommended by her father, steel guitarist Lloyd Maines, who had played on the band's earlier albums; she replaced Laura Lynch as lead singer.
Q 20Which Dixie Chicks single, written by Dennis Linde, has two friends poison an abusive husband?
Goodbye Earl
'Goodbye Earl' has best friends Mary Ann and Wanda poison Earl's black-eyed peas; the band Sons of the Desert had recorded it first, but their version was never released.
Fancy
'Fancy' first charted for Bobbie Gentry in 1969; in the lyric the dying mother spends her last money on the dress and a locket engraved 'To thine own self be true'.
Q 24George Strait began singing country in an Army band while stationed in which state?
Hawaii
Hawaii is where Strait, an Army enlistee, auditioned in 1973 and won the singer's spot in a country band on base; back home he studied agriculture and kept performing.
Q 25What is the singer's nickname?
The King of Country Music
The King of Country Music is his standing nickname, earned across forty years of number one singles and arena tours with his Ace in the Hole Band; the title had belonged to Roy Acuff before him.
Q 26In which 1992 film did George Strait play the lead?
Pure Country
Pure Country cast him as Dusty Chandler, a star who walks away from his overblown stage show; its soundtrack went on to become the biggest-selling album of his career.
Q 27In which state was George Strait born?
Texas
Texas: born in Poteet and raised in Pearsall, he played in a high-school rock garage band inspired by the Beatles before he ever sang country.
Q 28Where was Alan Jackson born?
Newnan, Georgia
Newnan, Georgia, is where Alan Jackson was born in 1958; after moving to Nashville in the mid-1980s he worked in the mailroom of The Nashville Network while honing his songwriting.
Q 29In Alan Jackson's 'Midnight in Montgomery', the singer visits a grave and meets the ghost of which country legend?
Hank Williams
Hank Williams died on New Year's Day 1953 on the way to a show and is buried in Montgomery, Alabama; the song has Jackson stop at the grave on New Year's Eve.
Q 30Which Alan Jackson single, a 1993 number one, is named after a Georgia river?
Chattahoochee
'Chattahoochee', written with Jim McBride, won the CMA's Single and Song of the Year awards, and one of its lines gave Jackson's album its title, A Lot About Livin' (And a Little 'bout Love).