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Country

THE VOTES WERE IN. THE HALL OF FAME WAS WAITING. BUT TOBY KEITH WAS ALREADY GONE. Toby Keith left this world on February 5, 2024. The next morning, the industry learned the news: he had been voted into the Country Music Hall of Fame. The final ballots had been cast just 72 hours before he passed. He never knew he had finally reached the peak of his industry. But here is the irony: Toby wouldn’t have been surprised, and he wouldn’t have been phased. He was a man who spent his final months making jokes about his weight loss and singing songs that stared death in the face. His final bow wasn’t a cry for attention; it was a masterclass in dignity. He had spent his final years pouring his soul—and nearly $18 million—into the OK Kids Korral, a sanctuary for children fighting the same battle he was. He didn’t want a spot in a museum. He wanted to make sure no kid had to fight alone.

THE SONG NASHVILLE FEARED BECAME TOBY KEITH’S REVENGE — AND COUNTRY MUSIC NEVER LOOKED AT HIM THE SAME AGAIN

Before Toby Keith became one of country music’s most recognizable voices, before the stadium crowds, the patriotic anthems, the awards, and the unmistakable swagger, he was a songwriter fighting to be heard in a town that often tells strong-willed artists to soften their edges. Nashville has always loved confidence — but only when it can control it. And Toby Keith was not built to be controlled.

The story behind “How Do You Like Me Now?!” is more than the story of a hit single. It is the story of an artist reaching the end of his patience and deciding that if the industry would not open the door, he would kick it open with a song. For years, executives tried to reshape him. Mercury Records, by his own later accounts, pushed him toward a version of himself that felt less honest, less Oklahoma, less Toby. He had success early with “Should’ve Been a Cowboy,” a song widely remembered as one of the defining country hits of the 1990s, but success did not mean freedom.

That is what makes “NASHVILLE TOLD HIM NO FOR YEARS. SO TOBY KEITH WROTE ONE SONG THAT MADE THEM ALL REGRET IT.” such a powerful frame for his career. The phrase sounds dramatic, but the emotion behind it is real. Toby Keith was not simply chasing another radio hit. He was answering every room where someone had looked at him and said, in one way or another, “Not like that. Not your way.”

When Mercury reportedly rejected much of the project that would eventually become part of his next chapter, Keith did something few artists would have the nerve — or the money — to do. He bought the material back, walked away, and signed with DreamWorks. Even there, “How Do You Like Me Now?!” was not immediately embraced as the obvious single. According to later accounts, Keith personally pushed for the song after the first single struggled, even calling radio programmers himself to get it moving. The result was undeniable: the song spent five weeks at No. 1, and the album later earned ACM Album of the Year recognition.

What older country listeners understood immediately was that this was not just attitude for attitude’s sake. Beneath the grin, the guitar bite, and the pointed title, the song carried the familiar ache of being underestimated. Everyone who has worked hard, been dismissed, and quietly waited for the day their work would speak louder than someone else’s doubt could hear themselves in it. Toby Keith did not sing it like a man asking for approval. He sang it like a man who had stopped needing permission.

That is why “How Do You Like Me Now?!” still matters. It captured a turning point when Toby Keith stopped being merely a successful country singer and became a force with his own direction. After that song, his identity sharpened. He was bold, stubborn, humorous, patriotic, confrontational, sentimental when he wanted to be, and completely uninterested in becoming anyone else’s polished product.

In country music, some songs climb the chart. Others change the temperature of an artist’s entire career. “How Do You Like Me Now?!” did both. It made radio listen. It made Nashville reconsider. Most importantly, it gave Toby Keith the one thing every true artist eventually has to claim for himself: the right to sound exactly like who he was.

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HOLLYWOOD NEVER CAGED THE OUTLAW WHILE HE WAS ALIVE—AND NOW, 25 YEARS AFTER HIS PASSING, THEY’RE FINALLY PUTTING WAYLON JENNINGS’ NAME ON THE SIDEWALK. Waylon Jennings never needed Hollywood’s approval. Nearly 25 years after his death, Hollywood finally came looking for him. The Hollywood Chamber of Commerce has selected Waylon for the Walk of Fame’s Class of 2027. Among 32 honorees, he is the only person being recognized posthumously. He joins the Recording category alongside the Ramones, Grandmaster Flash, and Sia. Sam Elliott is also part of the class, a pairing that will probably make more than a few country fans smile. Waylon was inducted into the Country Music Hall of Fame in 2001. He died the following year, long before Hollywood placed his name on its famous list. Now the man who spent his career refusing to play by the industry’s rules will finally have a star on Hollywood Boulevard. It is a fitting honor. The painful part is that the crowd will be there, the cameras will be there, and Waylon will not. Fans have known he belonged there for decades.

WHILE OTHER STARS PLAYED SAFE ARENAS AT HOME, TOBY KEITH SPENT HIS FORTIES AND FIFTIES WALKING STRAIGHT INTO WAR ZONES TO SING FOR TROOPS YOUNG ENOUGH TO BE HIS KIDS. In 2002, Toby Keith was 41 and one of the biggest touring acts in country music. That spring he started boarding military transport planes instead. The first trip was Bosnia, Kosovo, Macedonia — three thousand troops. He came back the next year. And the next. At 42, Naples and Kosovo. At 47, seventeen shows in ten days across Afghanistan. Then April 2011. He was 49. Outside Baghdad, a missile hit a third of a mile from the stage he was minutes from walking onto. At another base, four mortars landed close enough that the crew waited it out in a bunker. He went back up and played. He was 50 the next spring at Kandahar, doing it again. Eleven overseas USO tours. Eighteen countries. More than 250,000 service members — most of them nineteen, twenty. Old enough to deploy. Young enough to be his kids. In 2014, at 52, the USO gave him its Spirit of the USO Award. He said he’d seen the hole Bob Hope left behind, and joked that as hard as he tried, he couldn’t bring Marilyn Monroe. He died February 5, 2024, at 62. His father was a veteran. That’s where the songs started. The eleven trips are where the rest of him went.

TOBY KEITH CALLED IT THE STUPIDEST SONG HE EVER HEARD, YET A SILLY PLASTIC CUP BECAME HIS MOST UNFORGETTABLE FAREWELL. The “Red Solo Cup” was dismissed by critics as one of the worst country songs ever to become a hit. Toby Keith beat them to it—he called it the stupidest song he’d ever heard. He wasn’t being modest. It’s a spoken-word ode to a disposable plastic cup. It’s the only single on the whole album he didn’t have a hand in writing. Business Insider put it on a worst-of-the-decade list. He knew all of it, and he cut it anyway. Here’s why that’s not the own-goal it looks like. Keith wrote or co-wrote nearly everything he ever released. He heard this one—two sets of brothers goofing around under a fake band name—laughed until he couldn’t breathe, and grabbed it before anyone else could. Then he did something a vain man never would: he brought all four writers into the studio to sing and play on it, so the record would sound like them, not him. That’s the part people miss when they sneer at it. The song was never pretending to be art. It knew exactly what it was—a dumb, happy thing built to make a room full of strangers grin at the same time. Country has always been allowed that. Toby just never needed the song to make him look serious. Then February 2024 came, and stomach cancer took him at 62. At the CMT Awards that April, they handed red cups to the whole audience, his family in the crowd, and lifted them together. A joke about a plastic cup, and a room full of people crying into one.

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Country

HOLLYWOOD NEVER CAGED THE OUTLAW WHILE HE WAS ALIVE—AND NOW, 25 YEARS AFTER HIS PASSING, THEY’RE FINALLY PUTTING WAYLON JENNINGS’ NAME ON THE SIDEWALK. Waylon Jennings never needed Hollywood’s approval. Nearly 25 years after his death, Hollywood finally came looking for him. The Hollywood Chamber of Commerce has selected Waylon for the Walk of Fame’s Class of 2027. Among 32 honorees, he is the only person being recognized posthumously. He joins the Recording category alongside the Ramones, Grandmaster Flash, and Sia. Sam Elliott is also part of the class, a pairing that will probably make more than a few country fans smile. Waylon was inducted into the Country Music Hall of Fame in 2001. He died the following year, long before Hollywood placed his name on its famous list. Now the man who spent his career refusing to play by the industry’s rules will finally have a star on Hollywood Boulevard. It is a fitting honor. The painful part is that the crowd will be there, the cameras will be there, and Waylon will not. Fans have known he belonged there for decades.

Country

WHILE OTHER STARS PLAYED SAFE ARENAS AT HOME, TOBY KEITH SPENT HIS FORTIES AND FIFTIES WALKING STRAIGHT INTO WAR ZONES TO SING FOR TROOPS YOUNG ENOUGH TO BE HIS KIDS. In 2002, Toby Keith was 41 and one of the biggest touring acts in country music. That spring he started boarding military transport planes instead. The first trip was Bosnia, Kosovo, Macedonia — three thousand troops. He came back the next year. And the next. At 42, Naples and Kosovo. At 47, seventeen shows in ten days across Afghanistan. Then April 2011. He was 49. Outside Baghdad, a missile hit a third of a mile from the stage he was minutes from walking onto. At another base, four mortars landed close enough that the crew waited it out in a bunker. He went back up and played. He was 50 the next spring at Kandahar, doing it again. Eleven overseas USO tours. Eighteen countries. More than 250,000 service members — most of them nineteen, twenty. Old enough to deploy. Young enough to be his kids. In 2014, at 52, the USO gave him its Spirit of the USO Award. He said he’d seen the hole Bob Hope left behind, and joked that as hard as he tried, he couldn’t bring Marilyn Monroe. He died February 5, 2024, at 62. His father was a veteran. That’s where the songs started. The eleven trips are where the rest of him went.

Country

TOBY KEITH CALLED IT THE STUPIDEST SONG HE EVER HEARD, YET A SILLY PLASTIC CUP BECAME HIS MOST UNFORGETTABLE FAREWELL. The “Red Solo Cup” was dismissed by critics as one of the worst country songs ever to become a hit. Toby Keith beat them to it—he called it the stupidest song he’d ever heard. He wasn’t being modest. It’s a spoken-word ode to a disposable plastic cup. It’s the only single on the whole album he didn’t have a hand in writing. Business Insider put it on a worst-of-the-decade list. He knew all of it, and he cut it anyway. Here’s why that’s not the own-goal it looks like. Keith wrote or co-wrote nearly everything he ever released. He heard this one—two sets of brothers goofing around under a fake band name—laughed until he couldn’t breathe, and grabbed it before anyone else could. Then he did something a vain man never would: he brought all four writers into the studio to sing and play on it, so the record would sound like them, not him. That’s the part people miss when they sneer at it. The song was never pretending to be art. It knew exactly what it was—a dumb, happy thing built to make a room full of strangers grin at the same time. Country has always been allowed that. Toby just never needed the song to make him look serious. Then February 2024 came, and stomach cancer took him at 62. At the CMT Awards that April, they handed red cups to the whole audience, his family in the crowd, and lifted them together. A joke about a plastic cup, and a room full of people crying into one.

Country

FOUR MONTHS AFTER LOSING THE LOVE OF HIS LIFE, A BLIND AND WHEELCHAIR-BOUND JOHNNY CASH RECORDED SIXTY FINAL SONGS BECAUSE HE KNEW STOPPING WOULD KILL HIM. The Man in Black passed away on September 12, 2003, at age 71. The official cause was complications from diabetes. But those closest to him said the truth was simpler — he never recovered from losing June. June Carter Cash, his wife of 35 years, had died just four months earlier. By then Johnny had lost most of his vision and could barely walk. Yet before she died, June whispered something to him that he obeyed like a sacred command. He repeated her words to producer Rick Rubin days later: “You have to keep me working — because I will die if I don’t have something to do.” What followed was one of the most haunting recording sprees in music history. Sixty songs in four months. A final public performance where he read a tribute to June he had written minutes before walking onstage. And one last song — finished just 22 days before he died — about a doomed man whose dying words were “Nearer, my God, to Thee.” He wasn’t recording an album. He was saying goodbye.