Toby’s career lasted over 30 years, during which he made hit after hit. Songs like “Should’ve Been a Cowboy” made him a country music icon.

The world of country music is saddened by the loss of one of its greatest stars, Toby Keith. He passed away peacefully at 62. Toby Keith was not just a singer; he was a legend whose songs touched millions of hearts and will always be remembered.

Keith was not only a major music star, he also ventured into businesses in the Chicago area.

Keith died on Monday after a 2022 stomach cancer diagnosis. He was 62.

“He fought his fight with grace and courage,” his official X account said in a statement on Tuesday. “Please respect the privacy of his family at this time.”

On Tuesday, US-99 host Drew Walker broadcasted clips from old interviews he did with Keith.

What an incredible life of music and service to the military and military families,” Walker said.

Keith’s long list of achievements include 20 number one songs country charts and more than 40 in the top ten. Many songs were dedicated to active military and veterans.

Keith was not only a major music star, he also ventured into businesses in the Chicago area. In 2012, he had a licensing agreement to open a bar in the Rosemont’s entertainment district.

“It was tough on me,” said Former country radio star Ramblin’ Ray. “I cried. He meant a lot to me. He was a good man.”

Rosemont Mayor Brad Stephens also shared his memories with Keith.

“Really soft-spoken guy, but really genuine,” Stephens said. “[He] said what he meant and meant what he said. True patriot and great American.”

Keith played many concerts in the Chicago area. In 2022, he had to cancel his appearance at the 33rd annual RibFest because of his cancer battle.