Toby Keith Songs Spanning His Illustrious Career In Country Music

Nearly three decades ago, Toby Keith released his debut single. Since then, he has spent his career moving forward with an outlaw swagger and even becoming a household name. Well, it was expected as he came to Nashville with some of the strongest material. Toby Keith songs fit just about every emotion – love, happiness, heartache, loss, and even a little bit of rage – that really struck a chord with its audience.

Play these hits below, and you’ll know what we’re talking about.

1. “Courtesy of the Red, White, and Blue (The Angry American)”

Shortly after the 9/11 terrorist attacks in 2001, Keith wrote “Courtesy of the Red, White, and Blue” that established his unwavering support to the American armed forces. It was inspired by what he thought would have been his father’s thoughts about the terrorist attacks.

2. “How Do You Like Me Now?!”

When Toby Keith almost didn’t make it into country music – and worse, was told his songs weren’t good enough – he considered giving up. Luckily, he landed a record deal with the now-defunct DreamWorks Nashville label and released “How Do You Like Me Now?!” – a song about a guy wondering if the girl who rejected him in high school still remembers him now that he is famous.

It became one of the biggest hits of his career – it was hailed the No. 1 Country Song of 2000 and was his first major crossover hit, peaking at No. 31 on the Billboard Hot 100.

3. “You Shouldn’t Kiss Me Like This”

The fourth and final single of How Do You Like Me Now!? The song is about two people falling in love after their first kiss also reached No. 1 on Billboard’s Hot Country Songs chart – where it spent three non-contiguous weeks. It also peaked at No. 32 on the Billboard Hot 100.

4. “I Wanna Talk About Me”

Keith is said to have invented country-rap, and “I Wanna Talk About Me” is one proof of that – a rhythmically spoken song about a man’s frustration in his lack of ability to communicate with his partner, who always talks about herself.

5. “Who’s That Man”

Keith was definitely raising a glass to toast to his success when he wrote “Who’s That Man,” a song about a man coming back home to where he used to live. There, he found his wife, children, and even their family dog – but his wife’s new husband has now taken his place. 

6. “Me Too”

Struggling to say the words “I love you” to your significant other? Keith surely knows how you feel, and he sings about such a dilemma in “Me Too.” The romantic ballad tells the tale of a man who is not so good with words that he instead performs actual tasks as a way to show his affection.

7. “American Soldier”

After performing about 160 shows over nine years via USO tours, Keith shows support for the American fighting men and women once again in the incredibly moving, patriotic anthem “American Soldier.”

8. “My List”

The song finds Keith ticking things off his list of duties and responsibilities but, in the end, decides to start living and make more time for his family. It rings true to the singer as he enjoys spending time with his family, including Toby Keith’s wife Tricia and their three children.

9. “Cryin’ for Me (Wayman’s Song)”

Written by Keith himself, the song is dedicated to his friend, jazz musician Wayne Tisdale who died after a two-year battle with cancer.

10. “A Little Less Talk and a Lot More Action”

Originally recorded by Hank Williams Jr., the song became a big hit of Keith – reaching No. 2 on Billboard’s Hot Country Songs chart.

11. “Whiskey Girl”

Keith stormed the top of the charts with a song about “the epitome of a redneck girl.” The track also appeared on Keith’s two-disc compilation album in 2008 called 35 Biggest Hits.

12. “I Love This Bar”

Keith describes a local bar’s patrons – including “winners, losers, chain smokers and boozers” in “I Love This Bar.” It then reached the top of the charts – but more importantly, it set off a new business for the singer: Toby Keith’s I Love This Bar & Grill.

13. “Should’ve Been a Cowboy”

Toby Keith scored his first No. 1 hit with “Should’ve Been a Cowboy.” It catapulted him into massive country stardom, launching a lengthy and fruitful career.

14. “American Ride”

Keith describes “American Ride” as a “song of the times” where the narrator lists off different politically oriented issues in the country – from illegal immigration to rising gasoline prices.

15. “Red Solo Cup”

The simple appeal of this party-hearty anthem made its music video go viral upon its release. To date, it spawned more than 60 million views on YouTube.

More Toby Keith Songs

Toby Keith has proven over and over again how much of a terrific artist he is. Here are some more of his songs that you need to check out.

How about you? What are your favorite Toby Keith songs?