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

Remembering the country icon.

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 Nashville 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 three decades that have passed since that debut, Keith provided fans with songs to fit just about every emotion – love, happiness, pain, loss and even a little bit of rage at a time when others in the United States were feeling the same emotion.

In 2021, Keith was diagnosed with stomach cancer. “Last fall I was diagnosed with stomach cancer,” Keith tweeted in 2022. “I’ve spent the last 6 months receiving chemo, radiation and surgery. So far, so good. I need time to breathe, recover and relax. I am looking forward to spending time with my family. But I will see the fans sooner than later. I can’t wait.”

On Feb. 6, a statement on his official website announced the sad news that Keith had passed away at age 62. “Toby Keith passed peacefully last night on February 5th, surrounded by his family. He fought his fight with grace and courage. Please respect the privacy of his family at this time.”

Here are 10 times that Toby Keith has tapped into the American consciousness with some of his best songs.

Editor’s note: A version of this article was originally published in 2017.

“Red Solo Cup” (2011)

After almost two decades on the chart, the singer found himself with perhaps his most unusual hit in the fall months of 2011 — and unlike most of his hits, it was one he didn’t write. This tribute to the Solo Cup Company’s most popular style of cup earned the singer sales of over two million and a top 10 on the Hot Country Songs. And, to quote the lyrics, that was excuse enough to “have a party.”
“My List” (2002)

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 for the Hot Country Songs No. 1 proved to be an emotional one for fans, with the husband depicted in the clip revealed to be a fireman.
“He Ain’t Worth Missing” (1993)

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 Hot Country Songs top 5 hit was a great example of that.
“As Good As I Once Was” (2005)

The 2006 BMI Song of the Year (and six-week Hot Country Songs topper) 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.
“Upstairs Downtown” (1994)

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 Hot Country Songs top 10 in a while, dust it off — you’ll be glad you did.
“Courtesy of The Red, White, and Blue (The Angry American)” (2002)

9/11 inspired many heartfelt songs, but almost no one had released a song that talked about the anger that Americans felt once they were past the initial fear and 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 topped the Hot Country Songs chart in the summer of 2002 and remained a crowd favorite.
“Wish I Didn’t Know Now” (1994)

Hindsight, as they say is 20/20, and this Toby Keith song (No. 2 on Hot Country Songs) 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 on his first album – yet another taste of what was in store for country music fans.
“I Wanna Talk About Me” (2001)

At a time when many were lamenting the changing of the sounds of country music, this Hot Country Songs 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.”
“Should’ve Been a Cowboy” (1993)

With over three million spins on country radio stations, this song was one of the most played tracks of the 1990s. In his first Hot Country Songs No. 1 hit, Keith crafted a lyric that paid tribute to Matt Dillon of Gunsmoke, as well as Roy Rogers and Dale Evans. This song would have worked by simply paying tribute to the storied 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 song’s release.
“How Do You Like Me Now?!” (1999)

Whether we want to admit it, there is often someone in our past that we secretly dream of proving wrong about our lives. It could be a former lover, a former boss or a teacher. In this 2000 Hot Country Songs No. 1, Keith (and the video) told the story of a guy proving to the former Homecoming Queen that he did exactly what he had always planned on doing. 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.

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Link to the source article – https://www.billboard.com/lists/best-toby-keith-songs/

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

“Red Solo Cup” (2011)

“My List” (2002)

“He Ain’t Worth Missing” (1993)

“As Good As I Once Was” (2005)

“Upstairs Downtown” (1994)

“Courtesy of The Red, White, and Blue (The Angry American)” (2002)

“Wish I Didn’t Know Now” (1994)

“I Wanna Talk About Me” (2001)

“Should’ve Been a Cowboy” (1993)

“How Do You Like Me Now?!” (1999)

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