Five of our favorite Toby Keith songs

Toby Keith

Toby Keith was born on July 8, 1961, in Clinton Oklahoma. Throughout his career, he would rile up critics, be loved by millions of fans, and would bring the country together with his patriotic masterpieces. Sadly, he would lose the fight against cancer on February 6, 2024.

The country superstar released his first album-1993’s Toby Keith and followed it up with Boomtown in 1994, Blue Moon in 1996, and Dream Walkin’ in 1997. All four of the albums earned Gold or higher certifications and produced several Top Ten singles, including his debut “Should’ve Been a Cowboy”, which topped the country charts and was the most-played country tune of the 90s.

Let’s take a look at some of our favorite songs by this country superstar.

5: “Courtesy of The Red, White, and Blue (The Angry American)

With more than 42 million streams on Youtube, it is no surprise Courtesy of the Red, White, and Blue is considered one of Keith’s best. 9/11 sparked many heartfelt songs about the tragic day, but nobody had released a song about the anger Americans felt after the attacks on American soil. The song was written to honor his father who was a military veteran himself.

“My father had begged me for years to go on USO Tours, and I was so busy -- we were doing 130 shows a year -- that I just didn’t have it in my schedule. Finally, he passed away in March [of 2001], and then 9/11 happened. I was like, “Now I have to go honor him.”

Keith says he wrote the song on the back of a Fantasy Football sheet and it took all of 20 minutes to write. After writing it Keith did not immediately record it and release it as a single, but after playing it at a military function a commander told him he needed to release it as a single.

4: “Wish I Didn’t Know”

Wish I Didn’t Know is a song Keith wrote and released in February of 1994 as the fourth and final single from his self-titled debut album. The song climbed to number two on the U.S Billboard Hot Country Songs chart.

In the song, the narrator talks about how he suspects his lover was cheating on him, and now that he found out his suspicions were right. The title lyric originates from the Bob Seger & the Silver Bullet Band song “Against the Wind.”

3: “I Wanna Talk About Me”

I wanna Talk about me is written by Bobby Braddock and was released by Toby Keith in August 2001 as the second single from Keith’s 2001 album Pull My Chain. The song would become his seventh Number One single on the US Billboard Hot Country Singles and Tracks Chart.

Braddock said he initially intended the song for Blake Shelton’s debut album, which he produced. Audience testing of the song did not return favorable results and Shelton’s label decided not to include it on the album.

Braddock recalled the spoken-word verse of Keith’s 1998 single “getcha Some” and pitched it to him.

Keith told Billboard magazine that he knew he would get “banged a little” for cutting the song. “They’re going to call it a rap, [although] there ain’t nobody doing rap who would call it a rap.

2: “Should’ve Been A Cowboy”

Should’ve Been A Cowboy was the most played country tracks of the 90s. In the song, Keith pays tribute to Matt Dillon of Gunsmoke, as well as Roy Rogers and Dale Evans. The song was bolstered by the Dallas Cowboys returning to the Superbowl just two weeks before the songs’ release.

1: “How Do You Like Me Now?!”

In the music video for How Do You Like Me Now?! it shows a guy proving to a former Homecoming Queen that he did exactly what he had always planned on doing, but this song was not about a random guy. There was a personal touch to the song as Keith terminated his contract with Mercury due to the fact that the label rejected several of his songs for a new album, including this one.

The smash-hit spent five weeks at Number One on the Billboard U.S. Hot Country Songs chart and was Keith’s first major crossover peaking at number 31 on the U.S. Billboard Hot 100.

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