Toby Keith on the Deadline That Almost Stopped His Career

Toby Keith didn’t get to where he is today by caving to any shred of self-doubt. He still has the same hunger to be the best in his craft that he had when he first started.

“I tell people pursuing anything in music, ‘Dream big, and go for it,’” Keith told on Wednesday (Dec. 12). “But try to be as realistic as you can.”

There was a time in Keith’s early career when it almost became a hobby. He was in his late ‘20s and signed with a record label that was going to shelve his first album before his career had a chance to begin. At the time, he told himself that if he didn’t get his big break by a certain age, he would have to find work elsewhere.

“I had an album, and I just believed in it to the point of asking the label to drop me, which is completely unheard of,” Keith said. “I got an album rejected, was really struggling and was in a tough spot. I asked, ‘Can I take my album with me? They said, ‘Well we’ve got a lot of money tied up in it, but I guess you could buy it.’ Nobody had ever asked.

“Everywhere I went I was writing songs, and even though I had no Nashville success or anything big enough to make a good living,” he adds, “I still believed in what I was doing, and I thought my songs were better than everybody at my level. I really did. I just always prayed that if I hadn’t made it by 30 years old that I was going to go do something else. Fortunately, it happened for me right at the 11th hour.”

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That 11th hour moment came in the form of an early morning phone call 18 days before Keith’s 30th birthday from Mercury records executive, Harold Shedd, who was interested in seeing him perform after hearing one of Keith’s demos. Shedd produced and worked with Alabama, K.T. Oslin, Kentucky Headhunters, Glen Campbell and others.

“He came to Oklahoma, heard me perform and signed me on the spot.”

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. This year, he staged a major tour to recognize the song’s silver anniversary, and his self-titled debut is celebrated with a special 25th-anniversary release titled Should’ve Been A Cowboy. The new compilation adds three vault tracks: “Tossin’ And Turnin’,” “I’ll Still Call You Baby” and “Daddy Mac.”

Keith added what kept him from throwing in the towel before his big break was having a staunch believability in his work and a higher power.

“It’s just a ridiculous belief in yourself and believability in what you’re doing,” Keith said. “I read a couple interviews back then, and the one common thread throughout those interviews was that I had said, ‘They may out-write me, but they won’t out-work me.’ So, the second that ‘Cowboy’ broke through, we just took off, taking advantage of striking while the iron was hot because I didn’t know there was going to be a future. I didn’t know there would be another hit.”

There were more. Including “Cowboy,” Keith has accumulated 32 No. 1s, 26 of which he co-wrote and 16 he wrote by himself. His latest release is the title song for Clint Eastwood’s new movie The Mule, “Don’t Let the Old Man In.” The song was inspired by a conversation Eastwood and Keith had over a golf game when Keith found out that Eastwood would be on the set of the new film on his 88th birthday.

“I asked him, ‘What keeps you going?’ He said, ‘I just get up every day and not let the old man in,’” Keith recalled. “It was just as much about Clint as it was the guy in the movie. He treated me like a son and was wonderful to me. That’s what songwriters do — give him a song. I wrote it, sent it to him and he called me right back and said, ‘I’m going to put this in the movie.’”

Keith’s “Don’t Let the Old Man In,” is an intimate and haunting performance that’s full of drama. In theaters now, The Mule follows a 90-year-old horticulturist and WWII veteran who gets caught transporting $3 million worth of cocaine through Michigan for a Mexican drug cartel.

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Lauren Tingle is a Tennessean and storyteller who eats music for breakfast, lunch and dinner. When she’s not writing or rocking out, she enjoys yoga and getting lost in the great outdoors.