Toby Keith turned into a household name in 2002 when he sang “Courtesy of the Red, White, and Blue (The Angry American).” Nearly a decade after, he became a regular in the country charts. His career keeps moving forward with an outlaw swagger that suggests he’s one of the best cowboys in contemporary country music.

Let’s get to know more about Oklahoma’s very own Toby Keith!

He’s Already a Fan of Country Music At A Young Age

Toby Keith, who was born Toby Keith Covel in Clinton, Oklahoma, on July 8, 1961, started taking up guitar lessons when he was only eight years old. Growing up on a farm in Moore, near the outskirts of Oklahoma City, he would listen to his father’s Bob Wills records and fell in love with Merle Haggard’s music. He was also inspired by the country musicians who played at the supper club his grandmother ran.

His First Gig Was At A Wedding

While in high school, Toby Keith worked as a rodeo hand. After graduation, he found work in the oil industry. At the same time, he worked on the side as a musician. One of his first gigs was at a wedding where he made $1,000 that evening. That was something he referred to as “easy money.” He then formed his first band, the Easy Money Band, and played Alabama-style country-rock in honky-tonks. 

After about three years, the oil industry hit a major downturn. The future country star turned to playing semi-pro football for a USFL farm team. He even tried out for the short-lived league’s Oklahoma City franchise but did not get in. Toby Keith actually graduated from Moore High School, where he played defensive end on the football team.

Following two years as a football player, Toby Keith decided to focus more on music and adopted a much demanding touring schedule. Though he cut a few records for local indie labels, success did not come easy for him. 

He Almost Did Not Make It Into Country Music

During Toby Keith’s talk at the 2017 Country Radio Seminar, the Songwriters Hall of Fame member recounted his early days of trying to succeed in Music City, and how he considered giving up before he even got a record deal. This happened after one industry executive told him that his songs were not good enough.

“I had a meeting with Jimmy Bowen at Capitol. When I went in there and played, it was on a cassette, and he was just hitting fast forward. He’d play a verse and a chorus, and he’d hit fast forward,” Keith recalled. “We got done, and he goes, ‘Well, that’s all good and fine. You sing good, but you need to go back to the woodshed and work on your songwriting. These songs aren’t going to cut it.'”

Luckily, a friend believed in Keith, and that was enough to give his music to producer and record label head Harold Shedd, who asked to meet the singer and hear his songs live. Shedd signed Keith to Mercury Records. “He came to Oklahoma, heard me perform, and signed me on the spot,” Keith said.

From there, Keith’s debut single “Should’ve Been a Cowboy” from his self-titled debut went on to become his first of many signature songs. 

In Fact, He Credits His Entire Career to ‘Should’ve Been a Cowboy’

Toby Keith earned a No. 1 hit with “Should’ve Been a Cowboy,” when it was released in 1993. The country star went on to score a lot more chart-topping singles, release over a dozen hit records, and tour all over the world. But according to Toby Keith, none of that would have likely ever happened if he hadn’t written and released “Should’ve Been a Cowboy.”

“I know one thing, this song – everything I’ve done in my catalog, and I’ve recorded hundreds of songs I wrote and probably charted somewhere along a hundred or more – none of them probably would’ve ever been heard if it hadn’t been for ‘Should’ve Been a Cowboy,'” he said.

Toby Keith has already released twenty studio albums and seven compilation albums. He has released over 60 singles, with 65 of them charting on the Billboard country charts.

He Married His Wife Before He Became A Big Star

Toby Keith caught the attention of his wife, Tricia Lucus, when they first met at an Oklahoma nightclub in 1981. They danced together and started dating shortly after.

“I was 19, and he was 20,” Tricia told People. “He was just one of those larger-than-life guys, full of confidence.”

After dating for three years, the couple got hitched on March 24, 1984. Keith has adopted Shelley, Tricia’s daughter from a previous marriage too. A year after their wedding, they welcomed their daughter, Krystal. Their son Stelen arrived years later, in 1997.

The early years of their marriage were a bit tough. They were juggling raising a family while the creditors were chasing them. “He’d say, ‘Trish, one of these days, my time is coming. Hang in there,'” Tricia revealed.

But Toby Keith’s wife remained by his side until his career reached new heights. “Dozens of people told Tricia, ‘You need to go tell your old man to get a real job,'” the singer told Country Weekly. “It took a strong-hearted and loving woman to say, ‘He’s good enough at music that I’ve got to let him try. And it’ll be a great shot for both of us if he can make it work.'”

Toby Keith and Tricia continue to live in Oklahoma with their children and grandchildren nearby.

He Admits To Shaving His Armpits

You might not believe it, but the tough country star has admitted that he shaves his armpits.

“On those summer tours, you get so hot and sweaty,” he said. “You just want to shave your head and get down like a swimmer, you know what I mean?”

He Has Only Won Two Out of 27 CMA Nominations

Keith has been nominated in Country Music Association Awards 27 times but has won only two. He won one for video of the year in 2005 and another one for the male vocalist of the year in 2001. After he went home empty-handed in 2003 and 2004, despite receiving a total of 13 nominations, Keith told reporters he was done with the show. He also accused the CMA of playing politics.

“I haven’t been to a CMA Awards show in four years. They screwed me’ till I finally saw the light,” Toby Keith said.

From Easy Money To Being One of the Highest Paid Country Music Stars

Toby Keith is a regular on the list of the highest-paid country music stars, and country music stars with the highest net worth. That is because Toby Keith’s net worth is estimated to be about $345 million, while his total earnings surpass a whopping $500 million. 

In 2015, Toby Keith had an estimated annual income of $53 million.