A Look Back At Toby Keith's Deep Friendship With Clint Eastwood

Following Toby Keith's death in early February 2024, legendary actor Clint Eastwood took a moment to comment on the passing of the music icon. "Extremely Saddened by the passing of Toby Keith, Rest in peace my friend," Eastwood wrote on X, formerly Twitter. The short but sweet words were paired with a picture of the duo at the Los Angeles premiere of "The Mule," a notable event in their friendship.

The two icons became friends shortly before Eastwood began working on the 2018 movie. During a press conference, Keith shared how they met in a California community known for its resorts: "[Eastwood] is kind of a mascot at Pebble Beach, so I had been seeing him around," the Oklahoma native said, explaining that he was initially hesitant to approach the star. "As it went on, he kinda started coming up and speaking, and he puts the room at ease, so we became friends."

From there, Eastwood invited the country star to be his partner in a Carmel, California golf tournament. While the two became fast friends, they were also quick collaborators. Toby Keith's song "Don't Let The Old Man In" became personally significant following his stomach cancer diagnosis, but the idea for the tune actually came from Clint Eastwood.

It was during Toby Keith and Clint Eastwood's first-ever golf tournament together that the country star asked his friend about his ongoing inspiration. "I [asked], 'What keeps you going at your age?'" Keith shared during an interview with the "Superstar Power Hour" podcast. "He said, 'I try to get up every day and be productive — not let that old man in.'"

Throughout the three-day golf tournament, Eastwood also let his friends in on the plot of his upcoming movie "The Mule," which served as further inspiration for Keith's song. This film, both directed by and starring Clint Eastwood, follows a 90-year-old veteran turned drug cartel courier. "I didn't ask him if I could put a song [in the movie]," Keith said during his press conference. "I just went home and wrote it, sent it to him, and hoped that he would consider it. And, you know, he did."

The song, which contains poignant lines like "And I knew all of my life / That someday it would end / Get up and go outside / Don't let the old man in," is featured during the end credits of "The Mule." The moving tune is significant to his friendship with Eastwood, but it also became something of a personal anthem to the late country music star.

While undergoing treatment for his stomach cancer, Toby Keith broke his professional hiatus to perform his Clint Eastwood-inspired song "Don't Let The Old Man In" at the People's Choice Country Awards in Septemeber 2023. That same night, he was honored with the County Music Icon Award. While it turned out to be a tear-jerking performance, it almost didn't happen.

Keith revealed that he experienced an unexpected bought of sickness on the day of his televised performance. "I was pretty weak that day," he told Taste of Country, adding that he'd been feeling pretty good the days prior. "I went to dinner the night before and decided I would try to have a couple glasses of wine, and the next day, I was really down." Even so, Keith took the words of his song to heart, determined to make his special return to the stage.

"Showing up at this deal and singing that song — it just spotlighted the moment and the song so much," the singer said. "I had their attention, and then you dropped that heavy-hitting song on them, and it was just a magical moment." The feedback for the performance was so positive that Keith released the song as a radio single five years after its original creation. "Don't Let The Old Man In" is a testament to Keith's heartfelt friendship with Eastwood, but it also doubles as an emotional part of the star's enduring legacy.