Toby Keith performs during the 2021 iHeartCountry Festival at Frank Irwin Center on October 30, 2021 in Austin, Texas.
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Toby Keith Songs: The 20 Best By a Living Legend

Toby Keith rules country music with both humor and sentimentality.

Upon his 1993 debut single "Should've Been a Cowboy," Toby Keith rode into the country music spotlight as the genre's newest husky-voiced baritone singer and Music Row-ready wordsmith.

From there, he shone as a '90s "hat act" in the same era that brought us Tim McGraw and Kenny Chesney. At the turn of the century, Keith's high-energy material became the focus of a second chapter that also played up his lyrical sense of humor. Being the first name that comes to mind when it comes to 9/11 response songs because of "Courtesy of the Red, White and Blue (The Angry American)" made Keith a household name upon this career shift and still makes the Oklahoma native polarizing.

Heath concerns plus changes in what gets pushed as a country radio hit slowed down Keith's mainstream momentum in recent years, yet he still gets his flowers as one of the most compelling and consistent country stars of his time.

Here's Wide Open Country's 20 favorite Keith songs.

READ MORE: Toby Keith Through the Years: Look Back at His Life in Photos