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This 2000s country music trivia quiz has 50 free questions with answers and covers the decade from Shania Twain's Up! and the O Brother, Where Art Thou? soundtrack through Carrie Underwood's American Idol win, Taylor Swift's teenage debut, the Chicks' London controversy, Kenny Chesney's run of Entertainer of the Year awards, the MuzikMafia, Rascal Flatts, Keith Urban, Brad Paisley, Toby Keith, Sugarland, Lady Antebellum, Zac Brown Band and Johnny Cash's final chapter. Questions ask about artists, years, albums, chart peaks, writers and awards rather than lyrics, so they work for a bar trivia round, a road-trip playlist quiz or a Nashville-loving family night. Easy questions come first; the deep cuts will test people who remember which single hit number one in which year. Every answer was checked against encyclopaedia entries before publishing.
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Q 01Carrie Underwood won American Idol in 2005. Which numbered series of the show was it?
Fourth
Her debut Some Hearts became the best-selling solo female debut in country music, and 'Before He Cheats' was the first country song certified multi-platinum.
Q 02Carrie Underwood won which Grammy in 2007, only the second country act ever to take it?
Best New Artist
Garth Brooks inducted her into the Grand Ole Opry the following year.
Q 03Which pair co-hosted the CMA Awards every year from 2008 to 2018?
Brad Paisley and Carrie Underwood
Paisley had a streak of ten straight number-one hits from 2006 to 2009.
Q 04How old was Taylor Swift when she became the youngest CMA Entertainer of the Year in 2009?
19
Her album Fearless was that year's best-selling album in the US and went on to win the Grammy for Album of the Year.
Q 05Taylor Swift's self-titled debut album, released in October 2006, came out on which label?
Big Machine Records
She was 16 and wrote or co-wrote every track, the first female country artist to do that on a platinum debut.
Q 06Taylor Swift's debut single was named after which country star?
Tim McGraw
'Our Song' and 'Should've Said No' from the same album both went to number one on the country chart.
Q 07Which Taylor Swift album won Album of the Year at the 2010 Grammys?
Fearless
It also took Album of the Year at both the CMA and ACM awards, making it the most awarded country album in history.
Q 08In which city did Natalie Maines make her March 2003 comment about President Bush?
London
Their single 'Landslide' fell from number 10 to 43 on the Hot 100 in one week; the band dropped 'Dixie' from its name in 2020.
Q 09Which record won The Chicks Album of the Year in their five-Grammy sweep of 2007?
Taking the Long Way
'Not Ready to Make Nice', their answer to the backlash, won Song of the Year the same night.
Q 10Shania Twain's 2002 album Up! was unusual for being released in how many different musical versions?
Three
Country, pop and world/dance mixes; her 1997 album Come On Over remains the best-selling studio album by a female solo artist.
Q 11Which two illnesses forced Shania Twain into a long hiatus in the 2000s?
Lyme disease and dysphonia
The 'Queen of Country Pop' from Timmins, Ontario, later documented her vocal rehab on television.
Q 12At which awards show did Alan Jackson debut 'Where Were You (When the World Stopped Turning)' in November 2001?
The CMAs
He wrote it in one morning after waking at 4 a.m. with the melody; it won the Grammy for Best Country Song.
Q 13Johnny Cash's acclaimed 2002 cover of 'Hurt' was originally recorded by which band?
Nine Inch Nails
Trent Reznor said 'that song isn't mine any more' after seeing Mark Romanek's video; Cash died in September 2003, seven months after filming it.
Q 21Toby Keith wrote 'Courtesy of the Red, White and Blue' after 9/11 and which personal loss?
His father's death in a car accident
The Marine Corps commandant told him it was his duty to record it; ABC then dropped him from a Fourth of July special over its angry tone.
Q 22Toby Keith's 2003 duet 'Beer for My Horses', which spent six weeks at number one, featured which legend?
Willie Nelson
Keith launched his own label, Show Dog Nashville, in 2005.
Q 23Rascal Flatts' 'Bless the Broken Road' won which Grammy for 2004?
Best Country Song
Q 14Which award did the video for Johnny Cash's 'Hurt' win at the 2003 CMAs?
Single of the Year
The video also won the Grammy for Best Short Form Music Video and was later named the greatest music video ever by NME.
Q 15Who produced the O Brother, Where Art Thou? soundtrack that won the 2002 Grammy for Album of the Year?
T Bone Burnett
It sold more than eight million copies and was only the second soundtrack ever named CMA Album of the Year.
Q 16Who sang lead on 'I Am a Man of Constant Sorrow' as the voice of the Soggy Bottom Boys?
Dan Tyminski
Ralph Stanley's a cappella 'O Death' from the same soundtrack won him a Grammy for Best Male Country Vocal Performance.
Q 17Which artist won the CMA Entertainer of the Year award four times between 2004 and 2008?
Kenny Chesney
He also won four straight ACM Entertainer of the Year awards from 2005 to 2008 and named his fan club No Shoes Nation.
Q 18Which country star's brief 2005 marriage, annulled after four months, was to actress Renée Zellweger?
Kenny Chesney
They wed on the island of St. John in May and announced the annulment that September; he named his fan club No Shoes Nation.
Q 19Which country act won CMA Entertainer of the Year in both 2005 and 2006?
Keith Urban
The New Zealand-born, Australia-raised singer married Nicole Kidman in 2006; Billboard later named 'Somebody Like You' the biggest country hit of the decade.
Q 20The country star who married Nicole Kidman in 2006 was born in which country?
New Zealand
His family moved to Queensland when he was two, and he arrived in Nashville in 1992.
The Columbus, Ohio trio of Gary LeVox, Jay DeMarcus and Joe Don Rooney also had 2006's second-best-selling album, Me and My Gang.
Q 24Rascal Flatts recorded a cover of 'Life Is a Highway' for which 2006 Pixar film?
Cars
The same year 'What Hurts the Most' topped both the country and adult contemporary charts.
Q 25Gretchen Wilson's 2004 debut single, which went straight to number one, was called what?
Redneck Woman
It won her the Grammy for Best Female Country Vocal Performance and the CMA Horizon Award.
Q 26Gretchen Wilson, Big & Rich and Cowboy Troy were part of which Nashville songwriters' collective?
The MuzikMafia
Big & Rich's John Rich had earlier played bass in Lonestar.
Q 27Big & Rich's only number-one single, from 2007, was which song?
Lost in This Moment
'Save a Horse (Ride a Cowboy)' from their 2004 debut Horse of a Different Color peaked only at number 11.
Q 28When Garth Brooks announced his retirement in October 2000, what condition did he attach?
His youngest daughter finishing high school
He married Trisha Yearwood in December 2005 and began a Las Vegas residency at Wynn in 2009.
Q 29Which country singer did Garth Brooks marry in December 2005?
Trisha Yearwood
Brooks holds the record for the most Diamond-certified albums, nine, ahead of the Beatles' six.
Q 30Brad Paisley's 2004 duet 'Whiskey Lullaby' featured which bluegrass singer?
Alison Krauss
Paisley was inducted into the Grand Ole Opry in 2001 at age 28 and married actress Kimberly Williams in 2003.