Toby Keith Trivia
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49 free Toby Keith trivia questions with answers — music quiz, new questions added Oct 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 49 questions with answers and explanations. Play the quiz
Q 01Toby Keith grew up in Moore but was born in which small town in western Oklahoma?
Clinton
Clinton was only his birthplace: he was raised mostly in Moore, near Oklahoma City, and even at the height of his fame he kept his home in Oklahoma, outside Norman.
Q 02Toby Keith, Cyndi Lauper and the Grateful Dead's Jerry Garcia were all inducted in 2015 into which hall of fame?
Songwriters
Songwriters Hall of Fame entry suited a singer who wrote or co-wrote most of his own hits, starting with a debut No. 1 that he wrote entirely on his own.
Q 03After high school, what job did Toby Keith work while playing bars at night?
Derrick hand in the oil fields
Derrick hand in the oil fields was his day job, and he worked his way up to supervisor before the oil bust of the early 1980s put him out of work.
Q 04Out of work in the early 1980s, Toby Keith tried out for the Oklahoma Outlaws of which pro football league?
USFL
USFL hopes ended when he failed to make the Outlaws, so he played semi-pro ball for their unofficial farm team, the Oklahoma City Drillers, while still fronting his band at night.
Q 05What was the name of the group Toby Keith formed with friends at age twenty to play Oklahoma roadhouses?
Easy Money
Easy Money worked the dance halls of Oklahoma and Texas through the 1980s, already playing Keith's own "Does That Blue Moon Ever Shine on You", which became a hit for him in 1996.
Q 06Who slipped Toby Keith's demo tape to Harold Shedd, the Mercury Records producer who then signed him?
A flight attendant
A flight attendant who was a fan of his shows passed the tape on, after Keith himself had busked and knocked on doors along Music Row to no avail.
Q 07Which 2005 single gave Toby Keith six weeks at No. 1 on the country chart?
As Good as I Once Was
As Good as I Once Was plays his own aging for laughs: the narrator sits out a bar fight until pride drags him in, and in the video Keith ends the night knocked out cold.
Q 08The first verse of Toby Keith's "Should've Been a Cowboy" references which classic TV Western?
Gunsmoke
Gunsmoke was on Keith's mind in Dodge City, where the show is set: a friend there was refused a dance that a young cowboy then got, and someone joked he should have been one.
Q 09Toby Keith's "Should've Been a Cowboy" became a staple over the PA after games at which school?
Oklahoma State
Oklahoma State's teams are the Cowboys, hence the song. Keith, a die-hard fan of rival Oklahoma, once watched OSU rout his Sooners and heard it played on a loop as he left 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
Sting's own single had stalled near the foot of the Hot 100 a year earlier; the remake with Keith outdid it on the pop chart and became the only country hit Sting ever had.
Q 11Toby Keith sang lead on a 1996 remake of "Be True to Your School" backed by which band, its original hitmakers?
The Beach Boys
The Beach Boys made a whole album this way, Stars and Stripes Vol. 1: country singers took the lead vocals on the band's old hits while the band itself sang the harmonies behind them.
Q 12Which Toby Keith song was Billboard's No. 1 country song of the year for 2000?
How Do You Like Me Now?!
How Do You Like Me Now?! sat on an album Mercury turned down; Keith bought the recordings back, took them to DreamWorks, and the song spent five weeks at No. 1.
Q 13Which patriotic Toby Keith single topped the country chart for four weeks in early 2004?
American Soldier
Q 21Toby Keith's 2003 album title Shock'n Y'all puns on a slogan for the opening air assault of which war?
The Iraq War
The Iraq War opened in March 2003 with a bombardment billed as "shock and awe"; Keith said the phrase was on television so constantly that giving it a little country humour made sense.
Q 22Toby Keith's restaurant chain took its name from which of his songs?
I Love This Bar
I Love This Bar spent five weeks at No. 1 in 2003, and its success led to Toby Keith's I Love This Bar & Grill, a chain that spread to cities across the country before it collapsed.
Q 23Frank Capri, who took Toby Keith's restaurant chain nationwide, turned out to be what?
An ex-mobster
American Soldier was his thank-you to the troops he had met while playing for them overseas, and to the families who had brought him their support.
Q 14Which spoken-word Toby Keith No. 1 by Bobby Braddock was originally meant for Blake Shelton?
I Wanna Talk About Me
I Wanna Talk About Me was written for Shelton's debut album, but his label passed on it, so Braddock took the half-spoken number to Keith.
Q 15Whose gentler 9/11 song beat Toby Keith's angry anthem to the 2002 CMA Single of the Year award?
Alan Jackson
Alan Jackson's "Where Were You (When the World Stopped Turning)" came to him in the night: weeks after the attacks he woke at 4 a.m. with the song in his head, got out of bed and sang it into a recorder.
Q 16Toby Keith said he wrote "Courtesy of the Red, White and Blue (The Angry American)" in how long?
20 minutes
20 minutes was all it took, he said: the song poured out soon after the September 11 attacks and was also his answer to losing his father, an Army veteran, earlier that year.
Q 17After Toby Keith sang his angry post-9/11 song for Pentagon brass, who told him to release it?
Marine Corps Commandant James L. Jones
Marine Corps Commandant James L. Jones told him a singer could serve without suiting up for combat, because troops live on morale; until then Keith had sung it only at shows for the military.
Q 18Which news anchor did Toby Keith blame for dropping him from ABC's 2002 Fourth of July special?
Peter Jennings
Peter Jennings drew a retort Keith gave the press, "Isn't he Canadian?"; ABC's own account was that the network simply didn't 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
Saddam Hussein shared the screen with Maines after she called Keith's 9/11 anthem ignorant; she hit back at the 2003 ACM Awards in a T-shirt lettered "FUTK".
Q 20Which Toby Keith duet gave Willie Nelson, at 70, his first No. 1 country hit since 1989?
Beer for My Horses
Beer for My Horses spent six weeks at No. 1 in 2003, and Keith later spun it into a feature film of the same name, co-writing the script and playing the lead himself.
An ex-mobster, he had been a soldier in New York's Lucchese crime family before turning government witness; Capri was the new name witness protection gave him, and he used it to bilk developers.
Q 24Toby Keith recorded a cover of Inez and Charlie Foxx's "Mockingbird" in 2004 as a duet with whom?
His daughter Krystal
His daughter Krystal, then a teenager, sang it with him at the 2004 CMA Awards and wanted to head straight for Nashville, but he insisted she finish college before making records.
Q 25Which record label did Toby Keith found in 2005 after his years with DreamWorks?
Show Dog Nashville
Show Dog Nashville put him in business for himself once DreamWorks was absorbed by Universal, and he went on to release his last ten studio albums on his own label.
Q 26In 2005 Toby Keith bought a stake in which fledgling record label, which went on to launch Taylor Swift?
Big Machine Records
Big Machine Records began life sharing staff with Keith's own new label, and the stake he bought in it paid out handsomely: he earned whenever Swift did.
Q 27Which business magazine put Toby Keith on its cover in 2013 as country music's $500 million man?
Forbes
Forbes reckoned his career earnings had passed $500 million and that he had out-earned Jay-Z and Beyoncé that year, with a restaurant chain, a liquor brand and a record label beside the music.
Q 28Toby Keith made his film debut as a faded country singer who goes home to Tennessee in which 2006 drama?
Broken Bridges
Broken Bridges sends his character home for a brother's funeral, where he meets his high-school sweetheart again and has to face the past he walked away from; Kelly Preston and Burt Reynolds co-star.
Q 29Which comedian co-wrote and co-starred in Toby Keith's 2008 comedy film based on one of his duets?
Rodney Carrington
Rodney Carrington played his fellow deputy on a rescue mission to Mexico; the song had been a No. 1 hit, but the film drew a 0% score from critics on Rotten Tomatoes.
Q 30Which 2011 single, written by two pairs of brothers rather than Toby Keith, reached No. 15 on the Hot 100?
Red Solo Cup
Red Solo Cup struck Keith as the stupidest song he had ever heard, yet he was soon singing it in his head and could not get it out.