Toby Keith, the controversial and hugely successful country star who became an avatar for George W. Bush-era American masculinity, has died. According to a statement on his website, Keith passed away last night while surrounded by family. He was diagnosed with stomach cancer in 2022. He was 62.

Toby Keith was born Toby Keith Covel in Clinton, Oklahoma, and he mostly grew up in the suburbs outside Oklahoma City. Keith played high school football and then worked on Oklahoma oil fields. He and a few friends started a group called the Easy Money Band, and they played local bars in their spare time. After being laid off his oil job, Keith played semi-pro football, and the Easy Money Band began to tour through the Southwest. In the early ’90s, Keith went to Nashville and recorded a demo, and after a long struggle to be heard, he signed with Mercury.

Toby Keith’s 1993 debut single “Should’ve Been A Cowboy” became a #1 hit on the Billboard country chart, and it became one of the most-played country hits of the ’90s. Keith cut an intimidating figure — tall and barrell-chested, with an outsized swagger. He sounded like he’d seen some things, but his voice conveyed a soulful vulnerability that wasn’t always obvious in his lyrics.

In the ’90s, Keith jumped from one Nashville label to another. He released four platinum albums, and his singles “Who’s That Man” and “Me Too” went #1 country. In 1997, Keith covered Sting’s song “I’m So Happy I Can’t Stop Crying,” which was just a year old at the time. Sting appeared on the record, and the two of them performed together at the CMA Awards.

In 1999, Toby Keith signed to Dreamworks, and his album How Do You Like Me Now?! reshaped his image slightly, moving him away from glossy and romantic mainstream country and into a sort of hellraiser provocateur mode. The pose was knowingly exaggerated, and Keith’s videos became cartoonishly crass. The move was hugely successful. The album went platinum, and two of its singles went to #1. Keith did even better with 2001’s Pull My Chain, which went double platinum and sent three singles to #1.

Toby Keith achieved new levels of mainstream visibility with his 2002 single “Courtesy Of The Red, White And Blue (The Angry American),” a jingoistic and bloodthirsty response to the 9/11 attacks. The song became a #1 hit, and it reached #25 on the Hot 100 and turned Keith into a culture-war figure. Keith referred to himself as a “conservative Democrat,” and he endorsed George W. Bush’s reelection campaign. Later, he said positive things about both Barack Obama and Sarah Palin, and he eventually re-registered as an independent. In public, though, Keith played the role of right-wing tough guy, feuding with the Dixie Chicks and playing Donald Trump’s inauguration.

That right-wing move led to the peak of Toby Keith’s career. Two of his albums, 2002’s Unleashed and 2003’s Shock’n Y’all, went quadruple platinum. “Beer For My Horses,” his 2003 duet with Willie Nelson, endorsed vigilante justice and even lynching, and it became yet another country chart-topper. Even during this period, though, Keith hits were often just self-deprecating party songs like “As Good As I Once Was.” I reviewed a 2007 Toby Keith show in New Jersey, and I’m not quite sure what I expected. Keith’s set didn’t do anything to make my feelings about him less complicated, but he did know how to put on a show. He also talked a lot about how being an American didn’t mean being a Democrat or a Republican — the kind of talk that you really don’t hear from people in his cultural position anymore.

Toby Keith never again hit the zeitgeist the way that he did in his post-9/11 peak, but he kept racking up country hits for years; “Made In America,” his last #1, came out in 2011. Keith founded his own Show Dog Nashville imprint, and he opened a few branches of his I Love This Bar & Grill chain. Keith made multiple appearances on The Colbert Report and Huckabee, and he participated in a few TNA Wrestling events, once suplexing Jeff Jarrett. He starred in the made-for-cable movies Broken Bridges and Beer For My Horses, the latter of which was based on his song.

Keith contributed the song “Don’t Let The Old Man In” to the soundtrack of the 2018 Clint Eastwood film The Mule. Last year, at the Peoples Choice Country Awards, Keith performed that song, giving his first public appearance since his cancer diagnosis. He released Peso In My Pocket, his final album, in 2021, and he played his last live shows in December 2023 in Las Vegas. Below, check out some of Toby Keith’s work.