2000s Country Music Trivia
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This 2000s country music trivia quiz has 49 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.
30 of 49 questions with answers and explanations. Play the quiz
Q 01In Carrie Underwood's 'Before He Cheats', what smashes the cheating partner's headlights?
A baseball bat
A baseball bat, a Louisville Slugger in the lyric, does the damage; the song was first written with Gretchen Wilson in mind.
Q 02Carrie Underwood won which Grammy in 2007, only the second country act ever to take it?
Best New Artist
Best New Artist bore out Simon Cowell, who predicted during her American Idol run that she would outsell every previous winner; only LeAnn Rimes had taken the award for country before her.
Q 03Which pair co-hosted the CMA Awards every year from 2008 to 2018?
Brad Paisley and Carrie Underwood
Brad Paisley and Carrie Underwood hosted eleven ceremonies in a row; when the run ended, Underwood fronted one more with Reba McEntire and Dolly Parton, then stepped down.
Q 04Who, at 19, became the youngest CMA Entertainer of the Year in 2009?
Taylor Swift
Taylor Swift took the CMA's top prize only two years after touring as an opening act for George Strait.
Q 05Taylor Swift's self-titled debut album, released in October 2006, came out on which label?
Big Machine Records
Big Machine Records did not exist yet when Scott Borchetta saw Swift play Nashville's Bluebird Cafe; he offered her a place on the label he was about to start, and she signed in 2005.
Q 06LeAnn Rimes sang 'Can't Fight the Moonlight' for which 2000 film?
Coyote Ugly
Coyote Ugly gave the 17-year-old Rimes a cameo singing the song on top of the bar, and she supplied the heroine's singing voice for the rest of the film.
Q 07Which Taylor Swift album won Album of the Year at the 2010 Grammys?
Fearless
Fearless came back in 2021 as the first album Swift re-recorded, a project she began after the master recordings of her early albums were sold.
Q 08In which city did Natalie Maines make her March 2003 comment about President Bush?
London
London's Shepherd's Bush Empire was the venue, nine days before the invasion of Iraq; soon afterwards many American country stations stopped playing the band's records.
Q 09Which record won The Chicks Album of the Year in their five-Grammy sweep of 2007?
Taking the Long Way
Taking the Long Way was the trio's first studio album after the backlash over the Bush remark, and its lead single, 'Not Ready to Make Nice', answered the critics head-on.
Q 10Which star's 2002 album Up! came in pop, country and Indian film-music versions?
Shania Twain
Shania Twain colour-coded the discs: red for pop, green for country and blue for the Indian-style mix, which was sold mainly outside North America.
Q 11Which two illnesses forced Shania Twain into a long hiatus in the 2000s?
Lyme disease and dysphonia
Lyme disease and dysphonia kept her off stage for years: Twain says the infection damaged the nerves to her vocal cords, and she later had throat surgery to steady her voice.
Q 12Who debuted the 9/11 ballad 'Where Were You (When the World Stopped Turning)' at the 2001 CMA Awards?
Alan Jackson
Alan Jackson woke at 4 a.m. with the melody, finished the song that morning and sang it at the awards ten days later in place of the hit he had planned to perform.
Q 13Johnny Cash's acclaimed 2002 cover of 'Hurt' was originally recorded by which band?
Nine Inch Nails
Q 21Toby Keith wrote 'Courtesy of the Red, White and Blue' after 9/11 and the death of which relative, an Army veteran?
His father
His father, who had lost an eye serving in the Army, died in a car accident in March 2001; Keith meant the song only for live shows until the Marine Corps commandant told him it was his duty to record it.
Q 22Toby Keith's 2003 duet 'Beer for My Horses', which spent six weeks at number one, featured which legend?
Willie Nelson
Willie Nelson was 70 when the duet topped the chart, and five years later it grew into a comedy film starring both men.
Q 23Which Rascal Flatts ballad, a Grammy winner in 2006, was first recorded by the Nitty Gritty Dirt Band in 1994?
Bless the Broken Road
Nine Inch Nails' Trent Reznor feared the cover would be a gimmick, then saw the video and said the song wasn't his any more; Cash died seven months after filming it.
Q 14Johnny Cash's cover of 'Hurt' won which CMA award in November 2003, weeks after his death?
Single of the Year
Single of the Year honours the recording rather than the writing, so Cash could win it with a cover; he had died that September, less than two months before the ceremony.
Q 15Which 2000 film's old-time country soundtrack won the Grammy for Album of the Year in 2002?
O Brother, Where Art Thou?
O Brother, Where Art Thou? turned Depression-era folk, gospel and bluegrass into an eight-times-platinum album, and its singers filled Nashville's Ryman Auditorium for a concert film.
Q 16Which film star mimed 'I Am a Man of Constant Sorrow' on screen while bluegrass singer Dan Tyminski supplied the voice?
George Clooney
George Clooney was meant to sing it himself, but the producer had only two or three weeks to coach him, so Tyminski's vocal was dubbed in.
Q 17Alan Jackson's 2003 hit 'It's Five O'Clock Somewhere' was a duet with which singer?
Jimmy Buffett
Jimmy Buffett joined Jackson for eight weeks at number one, and the CMA trophy the duet won was the first award of his 30-year recording career.
Q 18Which country star's brief 2005 marriage, annulled after four months, was to actress Renée Zellweger?
Kenny Chesney
Kenny Chesney met Zellweger in January 2005 at a relief event for the Indian Ocean tsunami and married her that May on the Caribbean island of St John.
Q 19Who was the CMA's Male Vocalist of the Year three years running, from 2004 to 2006?
Keith Urban
Keith Urban's third win came while he was away in rehab: he entered treatment in October 2006 and completed it the following January.
Q 20The Australian-raised country star who married Nicole Kidman in 2006 was born in which country?
New Zealand
New Zealand's Whangārei was his birthplace; his drummer father gave him a ukulele at four, and his first guitar teacher came through an advert in the family shop window.
Bless the Broken Road waited a decade for its moment: co-writer Marcus Hummon and Melodie Crittenden both recorded it before Rascal Flatts took it to number one in 2005.
Q 24Gretchen Wilson's chart-topping 2004 debut single was called what?
Redneck Woman
Redneck Woman began, Wilson says, as she and co-writer John Rich watched a glamorous Faith Hill video and she remarked that she would never look like that; it spent five weeks at number one.
Q 25Gretchen Wilson, Big & Rich and Cowboy Troy were part of which Nashville songwriters' collective?
The MuzikMafia
The MuzikMafia began in 2001 as a Tuesday open-mic night in a tiny Nashville pub, held on what its founders called the worst night of the week; within three years it had launched Wilson and Big & Rich.
Q 26Which wedding ballad gave Big & Rich their first country number one in 2007?
Lost in This Moment
Lost in This Moment, sung by a groom at the altar, did what the duo's party anthem 'Save a Horse (Ride a Cowboy)' never managed: that one stalled at number 11.
Q 27Garth Brooks announced his retirement in October 2000 so that he could do what?
Raise his three daughters
Raise his three daughters: Brooks said he would stay away until the youngest was grown, and his comeback world tour duly began in 2014, the year she turned 18.
Q 28Which country singer did Garth Brooks marry in December 2005?
Trisha Yearwood
Trisha Yearwood said yes on stage: Brooks surprised her with a public proposal at Buck Owens' Crystal Palace in Bakersfield that May, and they married at home in Oklahoma in December.
Q 29Brad Paisley's 2004 duet 'Whiskey Lullaby' featured which bluegrass singer?
Alison Krauss
Alison Krauss sings the woman's half of the story; the song's darkest line began as a remark made to console co-writer Jon Randall after his divorce.
Q 30Which country star's 2004 crossover duet 'Over and Over' paired him with rapper Nelly?
Tim McGraw
It spent 10 weeks atop the top 40 chart; the same year he earned acclaim as an actor in Friday Night Lights.