Top 10 Most Iconic Toby Keith Songs

Arguably Toby's most iconic hit, Should've Been a Cowboy was written by Keith himself as one of his earlier songs. The lyrics talk about a man who fantasizes about living the life of a cowboy, inspired by the Western movies and TV shows he watched growing up. He imagines doing cowboy things such as riding horses, shooting guns, and romancing women like Annie Oakley and Jesse James' wife. He talks about how much fun it would be to live the life of a cowboy.

Another one of his earlier songs, How Do You Like Me Now?! is about a man who was rejected by a girl in high school. Years later, the man becomes famous and reflects on the girl who rejected him in high school, asking the question, How do you like me now? It's a song that a lot of people can relate to, trying to one-up an ex. Interestingly enough, the song is based on Keith's own experience of being snubbed by a girl who preferred more popular guys.

This song is undoubtedly one of Keith's most iconic songs. The song is a humorous and self-deprecating reflection on aging and masculinity, as Toby recounts various situations that test his physical and sexual prowess. It's not hard to see why this is a fan favorite.

Toby shows his witty and relatable songwriting style, and this is a song a lot of people can relate to.

This is a pretty humorous song where Toby sings from the perspective of men everywhere in a relationship where the woman just talks about everything. He lists all the different things that women will talk about and then he goes on to say, every once in a while, that they should talk about him. I could be wrong, but I feel like every man in the history of ever who's been in a relationship with a woman has had this feeling at one point or another.

Made in America would be Keith's last #1 song during his lifetime. This is definitely a Toby Keith anthem. The lyrics describe an American couple who is very patriotic. It talks about how the couple lives together and will only buy American products and support the USA, and how they're unhappy with the increase in foreign products in America. It's a passionate anthem that follows some of his other songs, and the lyrics are crafted well.

This song was released in response to the 9/11 terrorist attacks. It was the lead single in his "Unleashed" album. Some critics claim the lyrics promoted violence and nationalism, yet this song was a major hit.

The patriotic anthem definitely captures the retaliation feeling on most Americans' minds at the time. This song makes you feel very patriotic.

This country ballad reminds us to live in the moment and cherish those around us while we can. The message hits even deeper considering the song came out in 2002, a short time after the 9/11 terrorist attacks. People began to have a changed perception of life itself, realizing it's too short and unpredictable to waste.

This song does a great job of capturing that feeling.

One of Keith's all-time classics, his first major hit, featured another prominent country music singer, Willie Nelson. The song may come off as just a simple "Cowboys and Beers" song, but if you look beneath the surface, the lyrics talk about standing up for what's right and fighting injustices. Of course, this is done in a Wild West style where our narrators saddle up and round up the criminals themselves. This indirectly points out frustrations in the justice system for being ineffective. The song inspired a movie called "Beer for My Horses," starring both Keith and Nelson.

This song is a pretty witty and funny song. As the title implies, this song talks about the bar and why Toby likes the specific bar. He goes on to list all the different types of people who come to the bar and how they all make it a special place.

It's a drinking song that has even inspired a restaurant chain called I Love This Bar and Grill. Not many songs can claim that!