Toby Keith's Success and Achievements in Timeline

By Popular Timelines Editorial Team · Updated: February 22, 2025

A closer look at the biggest achievements of Toby Keith. Awards, milestones, and records that define success.

Toby Keith, born Toby Keith Covel, was a prominent American country music artist known for his singing, songwriting, and record production. He also ventured into acting and business. He was a significant figure in the country music scene, known for hits that often reflected patriotic themes and a distinctly American perspective. His career spanned several decades, leaving a lasting impact on the genre.

Sections (4)

Full Timeline Early Life & Education Career & Achievements Success & Recognition

1993: "Should've Been a Cowboy" reaches Number One

In 1993, Toby Keith's debut single, "Should've Been a Cowboy", reached number one on the U.S. Billboard Hot Country Songs chart, marking the beginning of his successful music career.

March 1997: "Me Too" becomes a Number One Hit

In March 1997, Toby Keith's song "Me Too" reached number one, marking his third number one hit.

2000: "How Do You Like Me Now?!" Success

In 2000, "How Do You Like Me Now?!" became the top country song and a pop hit, solidifying Toby Keith's success.

2000: "How Do You Like Me Now?!" Top Country Song

In 2000, Toby Keith's single "How Do You Like Me Now?!" was recognized as the number one country song, solidifying his place in the country music scene.

2001: ACM Awards

In 2001, Toby Keith won the Academy of Country Music's Top Male Vocalist and Album of the Year awards, recognizing his achievements in the country music industry.

2002: "My List" named Single of the Year

In 2002, the Country Music Association named Toby Keith's "My List" as Single of the Year, recognizing its success and impact.

March 2009: Received Johnny "Mike" Spann Memorial Semper Fidelis Award

In March 2009, Toby Keith received the Johnny "Mike" Spann Memorial Semper Fidelis Award for his support of the military, reinforcing his commitment to honoring service members.

December 2011: Named Artist of the Decade

In December 2011, Toby Keith was named "Artist of the Decade" by the American Country Awards, recognizing his contributions to country music.

July 15, 2013: Featured on Forbes magazine cover

On July 15, 2013, Toby Keith was featured on the cover of Forbes magazine with the caption "Country Music's $500 million man", highlighting his financial success.

January 13, 2021: Awarded National Medal of Arts

On January 13, 2021, Toby Keith was awarded the National Medal of Arts by President Donald Trump, recognizing his contributions to the arts.

September 28, 2023: Performance at People's Choice Country Awards

On September 28, 2023, Toby Keith performed publicly for the first time since his cancer diagnosis announcement in June 2022, receiving the Country Icon Award at the People's Choice Country Awards. He performed "Don't Let the Old Man In".

February 10, 2024: University of Oklahoma Honors Toby Keith

On February 10, 2024, the University of Oklahoma honored Toby Keith at a basketball game by handing out red Solo cups, inspired by his song.

March 2024: Posthumous Induction into Country Music Hall of Fame

In March 2024, one month after his death, Toby Keith was posthumously inducted into the Country Music Hall of Fame, having been elected shortly after his passing.