Toby Keith's 10 Best Songs: Critic's Picks

Toby Keith performs onstage at day 1 of the 2013 Stagecoach California's Country Music Festival at The Empire Polo Field on April 26, 2013 in Indio, Calif.
Christopher Polk/Getty Images for Stagecoach

Toby Keith performs onstage at day 1 of the 2013 Stagecoach California's Country Music Festival at The Empire Polo Field on April 26, 2013 in Indio, Calif.

Toby Keith came out from nowhere to become one of the major success stories of country music in 1993 with his debut single "Should’ve Been A Cowboy." The singer rode in from Oklahoma armed with some of the strongest material that the city had seen in quite some time. That helped his self-titled album to be certified Platinum – a sure sign of what was to come in his career.

In the twenty-four years that have passed since that debut, Keith has provided fans with songs to fit just about every emotion – love, happiness, pain, loss, and even a little bit of rage at a time where others in the United States were feeling the same emotion. Here are ten times that Toby Keith has tapped into the American consciousness with some of his best….

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10. Toby Keith - "Red Solo Cup"

A rarity in the instance that it’s one Toby Keith song that he did not write, this tribute to the Solo Cup Company’s most popular style of cups earned the singer his biggest selling hit ever – with sales of over two million. After almost two decades on the chart, the singer found himself with perhaps his most unusual hit in the fall months of 2011. And, to quote the lyrics, that was excuse enough….."To Have A Party."

9. Toby Keith - "My List"

The events of September 11, 2001 had everyone in the nation re-thinking their priorities in life. Toby Keith was no different than the average American in that sense. Recorded before the national tragedy, the video proved to be an emotional one for fans, with the husband in the clip’s job being revealed to be a fireman.

8. Toby Keith - "He Ain’t Worth Missing"

It’s worth noting that three of the songs on this list appear on his 1993 debut disc for Mercury, proving that the Oklahoma native came to town ready for the big time – as both a singer and a tunesmith. Even early on, Keith had found a way to say things in song that nobody else was saying, and this was a great example of that.

7. Toby Keith - "As Good As I Once Was"

The 2006 BMI Song of the Year was a realistic look at the masculinity behind the lead character in the song. Just like with many of Keith’s songs, this one was accentuated by the humorous video, which ended with a bar fight – and the singer being taken off in an ambulance. Ah, the life of a country music star!

6. Toby Keith - "Upstairs Downtown"

Keith brought an understated eloquence on this early hit about a woman embarking on her own path for the very first time. It came at a time when lyrical content was as critical as any other ingredient for a song to have success. If you haven’t heard this one in a while, dust it off. You’ll be glad you did!

5. Toby Keith - "Courtesy of The Red, White, and Blue (The Angry American)"

9/11 inspired many heartfelt songs that were very sentimental about how the events of that Tuesday morning had a tragic lean, but nobody had released a song that talked about the anger that Americans felt once they were past the initial fear and obvious sadness. Keith wrote the song as a tribute to his recently-deceased father. He performed it only in concert for awhile, until the Commandant of the Marine Corps convinced him it was his duty to record the track, in support of the troops. It’s remained a crowd favorite ever since.

4. Toby Keith - "Wish I Didn’t Know Now"

Hindsight, as they say is 20/20, and this Toby Keith song from his debut album told the story of a man who admits to having had his suspicions about his cheating significant other, and wishes he didn’t know now what he didn’t know then. The wordplay of the song was very impressive, particularly for a newcomer still on his first album – yet another taste of what was in store for country music fans.

3. Toby Keith - "I Wanna Talk About Me"

In a time period where many were lamenting the changing of the sounds of country music, this 2001 chart-topper struck many by surprise. With its’ strong beat and rhythmic lyrics, it was as close to a rap song on country radio as it got – which made the fact that it was written by Country Music Hall of Fame songwriter Bobby Braddock even more surprising – especially when you consider that his other major hits as a writer included "He Stopped Loving Her Today" and "D-I-V-O-R-C-E."

2. Toby Keith - "Should’ve Been A Cowboy"

With over three million spins on country radio stations, this song was one of the most played tracks of the 1990s. In his first hit, Keith crafted a lyric that paid tribute to Matt Dillon of Gunsmoke, as well as Roy Rogers and Dale Evans. The Toby Keith song would have worked by simply paying tribute to the old west, but it certainly didn’t hurt that the Dallas Cowboys had just returned to the Super Bowl less than two weeks before the songs’ release.

1. Toby Keith - "How Do You Like Me Now?!"

Whether we want to admit it or not, there has always been someone or something in our past that we have secretly dreamed of proving wrong about our lives. It could be a former lover, a former boss, or a teacher. In this 2000 career-defining performance, Keith allowed the video to show a guy proving to the former Homecoming Queen that he did exactly what he had always planned on doing, but this song was definitely personal for the singer. One of the reasons he asked to terminate his contract with Mercury was due to the fact that the label rejected several songs for a new album – with this one being one of them. Sometimes, he who laughs last in the music business laughs the loudest.