Country Superstar Toby Keith Dies at 62

He spent a couple seasons as a defensive end for the Oklahoma City Drillers, a farm team for the now-defunct United States Football League. But he found consistent money playing music with his band throughout the red dirt roadhouse circuit in Oklahoma and Texas.

“All through this whole thing, the only constant thing we had was music,” he said. “But it’s hard to sit back and say, ‘I’m going to go make my fortune singing music or writing music.’ I had no contacts.”

Eventually his path took him to Nashville, where he attracted the interest of Mercury Records head Harold Shedd, who was best known as a producer for the hit group Alabama. Shedd brought him to Mercury, where he released his platinum debut record, Toby Keith, in 1993.

“Should’ve Been a Cowboy,” his breakout hit, was played three million times on radio stations, making it the most played country song of the 1990s.

But the label’s focus on global star Shania Twain overshadowed the rest of the roster, and Keith felt that the executives were trying to push him in a pop direction.

“They were trying to get me to compromise, and I was living a miserable existence,” Keith told the AP. “Everybody was trying to mold me into something I was not.”

After a series of albums that produced hits like “Who’s That Man” and a cover of Sting’s “I’m So Happy I Can’t Stop Crying,” Keith moved to DreamWorks Records in 1999.

That’s when his multi-week “How Do You Like Me Now?!” took off and became his first song to cross over to Top 40 charts. In 2001, he won the male vocalist of the year and album of the year at the Academy of Country Music Awards, exclaiming from the stage, “I’ve waited a long time for this. Nine years!”

Toby Keith performs at the 46th Annual Academy of Country Music Awards on April 3, 2011 in Las Vegas.

Julie Jacobson/AP Photo

Keith often wore his politics on his sleeve, especially after the terrorist attacks on U.S. soil in 2001. Early on, he said was a conservative Democrat, but he later claimed he was an independent. He played at events for Presidents George W. Bush, Barack Obama and Donald Trump, the latter giving him a National Medal of the Arts in 2021. His songs and his blunt opinions sometimes caused him controversy, which he seemed to court.

His 2002 song, “Courtesy of the Red, White and Blue (The Angry American)” included a threat — “We’ll put a boot in your ass — It’s the American way” — to anyone who dared to mess with America.

That song got pulled from a patriotic ABC Fourth of July special after producers deemed it too angry for the show. Singer-songwriter Steve Earle called Keith’s song “pandering to people’s worst instincts at a time they are hurt and scared.”

Then there was the feud between Keith and The Chicks (formerly called the Dixie Chicks), who became a target of Keith’s ire when singer Natalie Maines told a crowd that they were ashamed of then-President George W. Bush. Maines had also had previously called Keith’s song “ignorant.”

Keith, who had previously claimed that he supported any artist’s freedom to voice their opinion about politics, used a doctored photo of Maines with an image of Saddam Hussein at his concerts, further ramping up angry fans.

Maines responded by wearing a shirt with the letters “FUTK” onstage at the 2003 ACM Awards, which many people believed was a vulgar message to Keith.

Keith, who acknowledged that he holds on to grudges, walked out of the ACM Awards in 2003 early because he had gotten snubbed in earlier categories, causing him to miss out when he was announced as entertainer of the year. Vince Gill accepted on his behalf. Keith came back the next year and won the top prize for a second year in a row along with top male vocalist and album of the year for Shock ’n Y’all.

His pro-military stance wasn’t just fodder for songs, however. He went on 11 USO tours to visit and play for troops serving overseas. He also helped to raise millions for charity over his career, including building a home in Oklahoma City for kids who are battling cancer and their families.

After Universal Music Group acquired DreamWorks, Keith started anew again, starting his own record label, Show Dog, in 2005 with record executive Scott Borchetta, who launched his own label Big Machine at the same time.

“Probably 75 percent of the people in this town think I’ll fail, and the other 25 percent hope I fail,” he said that year.

Later the label became Show Dog-Universal Music and had Keith, Trace Adkins, Joe Nichols, Josh Thompson, Clay Walker and Phil Vassar on its roster.

His later hits included “Love Me If You Can,” “She Never Cried In Front of Me,” and “Red Solo Cup.” He was inducted into the Songwriters Hall of Fame in 2015.

He was honored by the performance-rights organization BMI in November 2022 with the BMI Icon award, a few months after announcing his stomach cancer diagnosis.

“I always felt like that the songwriting was the most important part of this whole industry,” Keith told the crowd of fellow singers and writers.