A Timeline of Toby Keith’s Biggest Songs and Career Moments

Toby Keith first drew recognition beyond country music as the artist behind the divisive post-9/11 rallying cry “Courtesy of the Red, White and Blue (The Angry American).” But the singer-songwriter, who died Monday at the age of 62 after a battle with stomach cancer, appeared to view himself as a unifying force. “As far extreme as I seem,” he said in 2003, “I’m probably catching the average Joe in the middle better than anybody.”

Keith topped the country chart 20 times with a catalog of sturdily built anthems including those that romanticized the cowboy’s life and traded on the big-tent appeal of a favorite bar and the charms of drinking beer out of a “Red Solo Cup.” His robust voice was just as adept at conveying rueful heartache as it was at carrying riled-up swagger, and his surprisingly shaded political stances showed a similar range and savvy. Here’s a look back at some of his biggest hits and most prominent moments during a three-decade career.

Keith topped the U.S. country chart with his debut single, in which he longed for a life spent “wearing my six-shooter, riding my pony on a cattle drive,” and tipped his Stetson hat to legendary screen cowboys like Roy Rogers, Gene Autry and U.S. Marshal Matt Dillon of “Gunsmoke.” But the song was hardly the first rodeo for Keith, who had spent years playing the honky-tonk circuit in and around his native Oklahoma after high school. The 6-foot-4 musician also worked at an oil field — an experience that, he later reflected, “made a man out of me” — and played semipro football. He would come to view his winding path to success as a blessing.

“If I’d come out of the box with my first No. 1 hit at 21, instead of when I was 29, I probably wouldn’t have appreciated it because I wasn’t mature enough then,” he said in 2012.


After Keith’s then-label Mercury rejected his sixth album two separate times, he bought it back and sold it to DreamWorks. The company chose the somber “When Love Fades” as the first single, but the song foundered. Keith stepped in and suggested an alternative: the album’s defiant title track, a bold rejoinder to the girl who wouldn’t give him the time of day in high school. The song became his fourth country No. 1 and showed him the value of trusting his own instincts. “I said, ‘Man, you guys aren’t giving me a chance to fire my biggest missile,’” he later said of pushing for the swap. “So they pulled the single in five days, put out ‘How Do You Like Me Now?!’ and my career exploded.”

In the days after Sept. 11, Keith wrote this tough-talking battle cry of vengeance, American-style, in a sudden burst just one week after the attacks. The lyrics levied numerous threats against the perpetrators, none as indelible as Keith’s promise, backed by a solo-acoustic hush that is punctuated by a fiery full-band kick-in, that “you’ll be sorry you messed with the U.S. of A. / ‘Cause we’ll put a boot in your ass, it’s the American way.”

Keith originally envisioned the song as one he would perform exclusively for U.S.O. tours, but said he was swayed on a visit to the Pentagon when Gen. James L. Jones told him, “You have to release it. You can serve your country in other ways besides suiting up in combat.” In a time when many were denouncing George W. Bush’s war on terror, Keith was criticized for the song’s unapologetic jingoism, notably by Peter Jennings, who barred Keith from performing it on an ABC Fourth of July special. Keith retread the territory on the follow-ups “American Soldier” and “The Taliban Song.”


Keith’s anthem also drew the ire of the singer Natalie Maines of the Dixie Chicks (now the Chicks), who slammed it in a 2002 interview. “It’s ignorant, and it makes country music sound ignorant,” she said. “It targets an entire culture and not just the bad people who did bad things.”

Keith responded at his concerts by projecting a doctored image of Maines cozying up to Saddam Hussein. Maines clapped back by wearing a shirt featuring the initials “F.U.T.K.” to the 2003 ACM Awards. (At first she claimed the shirt wasn’t a dig at the “Angry American” singer, but in a 2006 documentary, admitted that it was. Keith eventually backed down, saying he was “embarrassed about the way I let myself get sucked into all of that.”


Keith topped the country chart again with this playful romp about the hard truths of aging — when it comes to romance, bar fights or all-purpose hell-raising — and the battle between humility and hubris. Inspired by a line that Keith’s friend and co-writer Scotty Emerick heard Burt Reynolds say, one which Keith’s father also favored (“I ain’t as good as I once was, but I’m as good once as I ever was”), the song offered a look at the star’s self-deprecating charm.

It would earn Keith his longest stay at the top of the country chart: six weeks, tied with “Beer for My Horses.” Shortly after the single’s release, Keith got in early on the trend of country singers opening bars when he launched his chain of I Love This Bar & Grill locations (riffing on an earlier hit: “I Love This Bar”).


Keith was never easy to pin down politically. Though his call for post-9/11 retribution seemed to peg him as right-leaning, he would later call himself a “lifetime Democrat,” who valued patriotism above all. In 2008, he spoke favorably about Barack Obama, praising the then-candidate’s trip to Afghanistan. “I think he’s the best Democratic candidate we’ve had since Bill Clinton,” Keith said. “And that’s coming from a Democrat.”


President Donald Trump had a tough time booking performers for his 2017 inauguration, but Keith showed up at a preconcert, playing “Courtesy of the Red, White and Blue” and dedicating the number to his father, who, as he sings early in the song, lost an eye while serving in the Army. Responding to the criticism around the performance, Keith said in a statement that “I don’t apologize for performing for our country or military. I performed at events for previous presidents Bush and Obama and over 200 shows in Iraq and Afghanistan for the U.S.O.” Speaking to The Atlantic, he said, more pointedly, that if “the president of the frickin’ United States asks you to do something and you can go, you should go.”

Keith first shared the news of his stomach cancer diagnosis in a June 2022 post on Instagram, reporting that he had already been receiving “chemo, radiation and surgery” for six months. After the release of his 19th, and final, studio album “Peso in My Pocket” (2021), Keith returned to the stage last year, playing two shows at Hollywood Corners, a former ’20s-era roadhouse in Norman, Okla., that he owned. He topped the country digital sales chart in October 2023 after an emotive performance of “Don’t Let the Old Man In” at the People’s Choice Country Awards.

Last December, he made his last live appearances during a three-night stint at the Park MGM in Las Vegas, and in January he opened up about the ordeal of his cancer battle. “It’s a lot of dark hallways,” Keith said.

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