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.

1993

‘Should’ve Been a Cowboy’

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.