Toby Keith, a hit country crafter of pro-American anthems who both riled up critics and was loved by millions of fans, has died. He was 62.

The “Should’ve Been a Cowboy” singer-songwriter, who had stomach cancer, died peacefully Monday surrounded by his family, according to a statement posted on the country singer’s website. “He fought his fight with grace and courage,” the statement said. He announced his cancer diagnosis in 2022.

Keith’s Career and Influence

The 6-foot-4 singer broke out in the country boom years of the 1990s, writing songs that fans loved to hear. Over his career, he publicly clashed with other celebrities and journalists and often pushed back against record executives who wanted to smooth his rough edges.

He was known for his overt patriotism on post 9/11 songs like “Courtesy of the Red, White and Blue,” and boisterous barroom tunes like “I Love This Bar” and “Red Solo Cup.” He had a powerful booming voice, a tongue-in-cheek sense of humor and range that carried love songs as well as drinking songs.

Among his 20 No. 1 Billboard hits were “How Do You Like Me Now?!,” “As Good As I Once Was,” “My List” and “Beer for My Horses,” a duet with Willie Nelson. His influences were other working class songwriters like Merle Haggard and he tallied more than 60 singles on the Hot Country chart over his career.

Throughout the cancer treatments, Keith continued to perform, most recently playing in Las Vegas in December. He also performed on the People’s Choice Country Awards in 2023 as he sang his song “Don’t Let the Old Man In.”

“Cancer is a roller coaster,” he told KWTV during an interview aired last month. “You just sit here and wait on it to go away. It might never go away.”

Keith’s Early Life and Career

Keith worked as a roughneck in the oil fields of Oklahoma as a young man, then played semi-pro football before launching his career as a singer.

“I write about life, and I sing about life, and I don’t overanalyze things,” Keith told The Associated Press in 2001, following the success of his song “I’m Just Talking About Tonight.”

Keith learned good lessons in the booming oil fields, which toughened him up, but also showed him the value of money.

“The money to be made was unbelievable,” Keith told the AP in 1996. “I came out of high school in 1980 and they gave me this job December of 1979, $50,000 a year. I was 18 years old.”

But the domestic oil field industry collapsed and Keith had not saved. “It about broke us,” he said. “So I just learned. I’ve taken care of my money this time.”

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 3 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 multiweek hit “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!”

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Keith’s Politics and Controversies

Keith often wore his politics on his sleeve, especially after the terrorist attacks on U.S. soil in 2001, and early on he said he was a conservative Democrat, but 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 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 had acknowledged that he holds onto 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. He 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.”

Went on 11 USO Overseas Tours

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 with 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% of the people in this town think I’ll fail, and the other 25% 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.