Keith — who won two American Music Awards (search) on Sunday night — has never strayed too far from his Sooner State roots, working long days in oil fields, playing semiprofessional football and raising racehorses.
"Most artists moved to Nashville," Keith said recently, lounging on a leather couch in his tour bus. "I never did have an address there. I was there for one day and never felt the need for more."
Instead of traveling to the Tennessee country music mecca, he honed his craft in the whiskey halls and bars of the Southwest for nearly a decade.
Keith began playing guitar at age 8 after receiving one for Christmas. later, he toured with his band Easy Money, in between playing semipro football for the Oklahoma Drillers and then a short stint with the Oklahoma Outlaws.
When the Outlaws failed and his football career was finally over, Keith put his energy into his music.
He toured 51 weeks a year, hitting honky tonks and music halls from Oklahoma to Texas to Colorado.
"It was the only way we could make enough money," he said. "Nothing ain't worth having if it's not worth fighting for. I was only going to do it for 10 years and it was getting pretty close."
But before he could quit and head back to the oil fields of Oklahoma, he got a deal with Mercury Records.
"They came to me," he says with a smirk.
Keith put out three albums with Mercury before switching to DreamWorks, which allowed him the freedom to record the witty, occasionally redneck lyrics that have become anthems for country fans and non-fans alike.
Keith doesn't mince words when describing Nashville and the industry he says has reluctantly embraced him. Despite nearly two dozen country award nominations, he's only taken home a handful (he was two for five on Sunday night).
In 2003, the Academy of Country Music named him Entertainer of the Year — but he wasn't there to pick it up. Thinking his chances were slim, he left the ceremony to work on a song with Willie Nelson.
"The awards are kind of like the All-Star game," Keith said. "You take your turn at bat, smile and give everybody the finger and leave."
That's Keith for you — honest and blunt. That grit translates into his drinking anthems, his ballads and his collection of post 9-11 patriotic songs.
Keith has written nearly all the songs he's recorded and says he writes when he gets the inspiration.
"I'll do it for five minutes here, or I'll be thinking about while I'm in the shower," Keith said. "I never could write by appointment."
Straightforward lyrics and edgy guitar riffs have given him staying power. "It was important everybody speak their mind," Keith said. "But if you're going to speak up, at least have something to say."
Recently, Keith's been talking about a lot more than music in his home state.
As a horseman, he championed a proposal recently approved by voters that expands casino-like gambling to the state's struggling horse racing tracks. Keith also stumped for a measure to create a lottery to fund public education.
"Everybody needs to try to make a difference and they have a responsibility to stay up on current events," Keith said. "I can be a difference-maker and I try to be."
Standing 6-foot-4 with blond curls peaking out from his weathered cowboy hat, Keith was frequently seen on the campaign trail this fall. He's supported several Democrats, including Oklahoma's Democratic Gov. Brad Henry.
"I campaign for my friends, people I can trust," said Keith, who is a registered Democrat in Oklahoma but nonetheless supported Republican President George W. Bush.
"I think Toby is passionate about Oklahoma and truly wants to make state a better place," Oklahoma's governor said. "Instead of sitting on the sidelines, he's gotten involved in issues he believes are important."
Keith is keeping his wealth in Oklahoma. He and his family live near Norman, home to Keith's beloved University of Oklahoma Sooners. His latest project is a $4.7 million restaurant and music hall in Oklahoma City's fledgling entertainment district, Bricktown.
The venture, "Toby Keith's I Love This Bar & Grill," will seat up to 600 people and is expected to be a stopping spot for touring acts. Keith recently opened a similar bar in Las Vegas and plans for bars in North Kansas City, Mo., and Shreveport, La., are in the works.
"It's a great chance to help support Bricktown and what they're trying to do down there," Keith said. "The whole concept reflects my passion for Oklahoma and where everyone will feel comfortable."