Inside Toby Keith's Relationship With Donald Trump

In the ever-growing controversy surrounding politics in the media, it's become harder and harder for celebrities to side on the sidelines and not give their opinion on current events. While some speak out against or in favor of certain political figures, others are determined to stay impartial regarding different sides of the aisle. Iconic country singer Toby Keith, who died on February 5, wasn't shy when it came to sharing his opinion on politics, and he didn't apologize if his actions came under criticism from fans.

The singer-songwriter rose to fame in the early 1990s when his first number-one single, "Should've Been A Cowboy," made him a household name in country music. He continued to release hit after hit, growing his fan base and steadily becoming one of the most recognized figures in the genre. Despite holding political values that fell more moderate than liberal or conservative, Keith's fans leaned more right than left. When the 2016 election came around, many fans wondered how Keith felt about both Hillary Clinton and Donald Trump. While Keith was not an outspoken supporter of former President Trump, he also didn't speak out against him, and the two appeared to be on reasonably good terms. 

Like many Americans, country singer Toby Keith was shocked and confused regarding the 2016 presidential election. Voters were surprised that Hillary Clinton and Donald Trump were the two biggest candidates battling for the presidency and were at a loss as to what to do. Keith found trying to choose between Clinton and Trump was a lose-lose situation and referred to the presidential race as a "dumpster fire" during a performance in 2016 (via Rolling Stone).

Keith continued, summing up the feeling of choosing between the two: "This is by far the best country you could ever live in and we picked these two candidates to be media whores and go out there and take care of the world, huh? You gotta pick one."

Keith also spoke to the Chicago Tribune about the impending 2016 election, and when asked which candidate would be a better choice, he responded: "This election, I don't think it makes a difference. I can't believe there's 300 million Americans in this country and we've got these two as our final two. It's absolutely crazy." Not quite a ringing endorsement for Donald Trump.

Despite Toby Keith's opinion that neither Hillary Clinton nor Donald Trump was the best choice for president in 2016, when Trump won the election, Keith took it in stride. It's no secret that Trump had a hard time finding artists to perform at his inauguration in 2017 and that many singers who were asked refused, but Keith accepted. Some fans were skeptical, taking Keith's performance at the inauguration as an endorsement of Trump, but the singer was not at all bothered by others' opinions.

"I don't apologize for performing for our country or military," he explained in a statement given to Entertainment Weekly in 2017. "I performed at events for previous presidents [George W.] Bush and [Barack] Obama and over 200 shows in Iraq and Afghanistan for the USO."

Keith was also honored by Trump in 2021 with the National Medal for the Arts along with Ricky Skaggs, Mary Costa, Nick Ut, and Earl "Rusty" Powell III. The presentation occurred at the same time that Trump was impeached as president for the second time. Keith's representatives gave no comment on the honor, although it was a milestone for Keith's historic career.