A Look Back: Toby Keith's Milestones and Career Highlights

Released his self-titled debut album in 1993, featuring the hit single "Should've Been a Cowboy," which topped the country charts.

Debut Album

Achieved mainstream success with his album "How Do You Like Me Now?!" in 1999, featuring the title track, which became his first number one hit on the country charts.

Breakthrough Success

Released "Courtesy of the Red, White and Blue (The Angry American)" in 2002, a patriotic anthem that became one of his signature songs and sparked controversy.

Patriotic Anthem

Established his restaurant chain, Toby Keith's I Love This Bar & Grill, and ventured into other business ventures, demonstrating his entrepreneurial acumen.


Produced numerous chart-topping singles throughout his career, including "Beer for My Horses," "American Soldier," and "As Good as I Once Was."

Multiple Chart-Toppers

Received multiple nominations and wins at the Country Music Association Awards, solidifying his status as a respected figure in country music.

CMA Awards

Known for his electrifying live performances, headlined stadium tours and captivated audiences with his energetic stage presence.

Live Performances

Established the Toby Keith Foundation, supporting various charitable causes, including pediatric cancer research and military support programs.


Founded Show Dog Nashville, his own record label, providing a platform for emerging country artists to showcase their talent.

Music Label

Toby Keith's enduring influence on country music and his contributions as a singer, songwriter, and philanthropist have secured his place as a prominent figure in the genre's history.

Enduring Legacy