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50 free Toby Keith trivia questions with answers — music quiz, new questions added Aug 2026.
This Toby Keith trivia quiz follows the whole arc of the Oklahoma singer's life, from the derrick hand who tried out for a USFL team to the Country Music Hall of Famer elected just hours after his death in 2024. It covers the demo tape a flight attendant handed to a producer, the 1993 debut single that still blares out of Oklahoma State's stadium, the song a label rejected before it became the top country hit of 2000, and the Willie Nelson duet that made Nelson the oldest artist ever to top the country chart. You will also find the feuds and side businesses: the Peter Jennings walkout, the doctored Natalie Maines backdrop, the restaurant chain that collapsed under an ex-mobster franchisee, the label he built after DreamWorks folded, his two films, his wrestling and Colbert cameos, and the golf-course conversation with Clint Eastwood that produced his final hit. About a third of the questions are easy enough for a casual country fan; the rest get into chart weeks, co-writers, video cameos and USO numbers that will test even someone who saw him at every stop of the Biggest and Baddest Tour. Every answer was checked against encyclopaedia entries for the man, his albums and his singles before it was published.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Toby Keith was born in 1961 in which Oklahoma town?
Clinton
His birth name was Toby Keith Covel; the family later settled in Moore, a suburb of Oklahoma City, where he played high-school football.
Q 02How old was Toby Keith when he got his first guitar?
Eight
He got hooked on music doing odd jobs at his grandmother's supper club, where he would climb onto the bandstand to play with the house band.
Q 03After high school, what job did Toby Keith work while playing bars at night?
Derrick hand in the oil fields
He worked up to supervisor and sometimes had to walk out mid-concert when he was paged back to the rig; the 1982 oil bust put him out of work.
Q 04After the oil bust, Toby Keith tried out for the Oklahoma Outlaws of which pro football league?
USFL
He did not make the roster but played defensive end for the team's unofficial semi-pro farm club, the Oklahoma City Drillers, while still gigging with his band.
Q 05What was the name of the group Toby Keith formed with friends at age twenty to play Oklahoma roadhouses?
Easy Money
The group played roadhouses across Oklahoma and Texas for most of a decade before Keith went to Nashville on his own.
Q 06How did Toby Keith's demo tape reach the Mercury Records producer who signed him?
A flight attendant who was a fan passed it on
Keith had been busking along Music Row without success before Harold Shedd heard the tape and signed him.
Q 07Which song was Toby Keith's debut single and first No. 1 country hit in 1993?
Should've Been a Cowboy
It was released on February 12, 1993, topped the country chart that June, and was certified three-times platinum thirty years later.
Q 08The first verse of Toby Keith's 1993 debut single references which classic TV Western?
Gunsmoke
The verse nods to Marshal Dillon never settling down with Miss Kitty; the chorus name-checks singing cowboys Gene Autry and Roy Rogers.
Q 09Toby Keith's debut single is a staple played over the PA after sporting events at which school?
Oklahoma State
The school's teams are the Cowboys, so the song is often played several times in a row as fans file out of the stadium.
Q 10Which rock star sang duet vocals and played bass on Toby Keith's 1997 cover of one of his own songs?
Sting
The cover of "I'm So Happy I Can't Stop Crying" reached No. 2, and the pair performed it together at that year's CMA Awards.
Q 11On the Beach Boys' 1996 album Stars and Stripes Vol. 1, Toby Keith sang lead on which of their hits?
Be True to Your School
The Beach Boys themselves supplied the harmonies and backing vocals on the now out-of-print country tribute album.
Q 12Which Toby Keith song was Billboard's No. 1 country song of the year for 2000?
How Do You Like Me Now?!
Mercury had rejected the song before Keith left the label; at DreamWorks it spent five weeks at No. 1 and became his first Top 40 pop hit.
Q 13Which underperforming single from his first DreamWorks album did Toby Keith ask to have withdrawn?
When Love Fades
Q 21The title of Toby Keith's 2003 album, a pun on a military term, ends in "Y'all". What is the term?
Shock and awe
All three singles from the album went to No. 1, and it also carried the live tracks "The Taliban Song" and "Weed with Willie".
Q 22Toby Keith's restaurant chain took its name from which of his No. 1 hits?
I Love This Bar
The first locations opened in 2005 in Oklahoma City, Tulsa and Syracuse; the song itself later made Rolling Stone's 200 greatest country songs list.
Q 23Frank Capri, who took Toby Keith's restaurant chain nationwide, turned out to be what?
An ex-mobster
Keith said DreamWorks executives were scared of the replacement, but within five days they pulled the single and released the title track instead.
Q 14Which spoken-word Toby Keith No. 1 by Bobby Braddock was originally meant for Blake Shelton?
I Wanna Talk About Me
Shelton's label dropped it after poor audience testing, so Braddock pitched it to Keith, remembering his earlier country-rap single.
Q 15Which Toby Keith single did the Country Music Association name Single of the Year in 2002?
My List
It was one of three straight No. 1s from the album Pull My Chain, two of which held the top spot for five weeks each.
Q 16Toby Keith said he wrote "Courtesy of the Red, White and Blue (The Angry American)" in how long?
20 minutes
It was a response to the September 11 attacks and to his father's death that March; he originally meant it only for live shows in front of troops.
Q 17Who told Toby Keith it was his "duty as an American citizen" to record his angry post-9/11 song?
Marine Corps Commandant James L. Jones
Keith had refused to record it and only sang it at concerts for military personnel until Jones talked him round.
Q 18Which news anchor did Toby Keith blame for dropping him from ABC's 2002 Fourth of July special?
Peter Jennings
Keith's retort was "Isn't he Canadian?"; ABC said the network simply did not want to open the show with an angry song.
Q 19Toby Keith's concert backdrop showed a doctored photo of Chicks singer Natalie Maines with whom?
Saddam Hussein
Maines fired back at the 2003 ACM Awards with a T-shirt reading "FUTK", which she later admitted on Bill Maher's show was aimed at Keith.
Q 20Which Toby Keith duet made Willie Nelson, at 70, the oldest artist ever to top the country chart?
Beer for My Horses
It spent six weeks at No. 1 in 2003 and was Nelson's first chart-topper since 1989; a Texas congressman later quoted a line from it thinking it was an old saying.
Lawsuits over the collapsed franchise left Capri and his companies owing tens of millions; he had used both Toby Keith and Rascal Flatts branded restaurants to defraud developers.
Q 24Toby Keith recorded a cover of Inez and Charlie Foxx's "Mockingbird" in 2004 as a duet with whom?
His daughter Krystal
It was Krystal's first chart entry; the two also sang it at that year's CMA Awards before Keith insisted she go to college.
Q 25What label did Toby Keith found on August 31, 2005, after DreamWorks Records shut down?
Show Dog Nashville
It merged with Universal South in 2009 to become Show Dog-Universal, and Trace Adkins was its first post-merger signing.
Q 26Toby Keith was a founding partner in which label, whose first signing was Taylor Swift?
Big Machine Records
Ex-DreamWorks executive Scott Borchetta launched it in September 2005, and it originally shared much of its staff with Keith's own label.
Q 27A 2013 Forbes cover story called Toby Keith "Country Music's ___ man". Fill in the figure.
$500 million
The article said he had earned $65 million in the previous 12 months, more than Jay-Z or Beyoncé, and at least $48 million a year for five years.
Q 28In his 2006 film debut Broken Bridges, Toby Keith played a washed-up country singer named what?
Bo Price
The film grossed only about $252,000 in theatres but sold over $8 million on DVD and was a CMT staple; Burt Reynolds and Kelly Preston co-starred.
Q 29Toby Keith co-wrote and starred in a 2008 comedy based on one of his duets. Who was his co-writer and co-star?
Rodney Carrington
Shot around Las Vegas, New Mexico, it earned a rare 0% on Rotten Tomatoes; Ted Nugent played a fellow deputy named Skunk.
Q 30Which 2011 single, the only Clancy's Tavern song Toby Keith did not write, became his highest Hot 100 hit at No. 15?
Red Solo Cup
Keith called it the stupidest song he had ever heard but also "freakin' awesome"; the video features Larry Bird, Roger Clemens and Ted Nugent.