Toby Keith’s Biggest Hits: From ‘Should’ve Been a Cowboy’ to ‘Red Solo Cup’:

Hey there, country music fans! If you’ve ever found yourself humming along to the catchy tunes of Toby Keith, then you know just how infectious his music can be.

In this article, we’re going to dive deep into some of Toby Keith’s biggest hits, from the iconic “Should’ve Been a Cowboy” to the party anthem “Red Solo Cup.”

So, grab your boots and let’s unpack the stories behind these unforgettable songs!

“Should’ve Been a Cowboy”: The Song That Started It All

Back in 1993, Toby Keith burst onto the country music scene with his debut single, “Should’ve Been a Cowboy.”

With its twangy guitars and catchy chorus, this song quickly became a fan favorite and catapulted Keith to stardom.

Inspired by classic Western films, “Should’ve Been a Cowboy” is a nostalgic tribute to the cowboy way of life, complete with dusty trails and wide-open plains.

“How Do You Like Me Now?!”: Toby Keith’s Revenge Anthem

In 1999, Toby Keith unleashed “How Do You Like Me Now?!” upon the world, and it became an instant anthem for anyone who’s ever felt underestimated or overlooked.

With its defiant lyrics and infectious groove, this song is a celebration of self-confidence and perseverance.

Whether you’re cruising down the highway or belting out the chorus at the top of your lungs, “How Do You Like Me Now?!” is guaranteed to get your blood pumping.

“Beer for My Horses” (with Willie Nelson): A True Country Collaboration

When Toby Keith teamed up with country legend Willie Nelson for “Beer for My Horses” in 2003, fans knew they were in for something special.

This rollicking anthem is all about justice, Texas-style, and it’s got everything you’d expect from a classic country song: twangy guitars, catchy lyrics, and plenty of attitude.

So, grab a cold one and raise a toast to the good ol’ boys who keep the peace in the Lone Star State!

“Courtesy of the Red, White, and Blue (The Angry American)”: A Patriotic Tribute

Few songs have captured the spirit of American pride quite like “Courtesy of the Red, White, and Blue (The Angry American).”

Written in the wake of the September 11th attacks, this powerful anthem is a tribute to the brave men and women who serve in the armed forces.

With its soaring chorus and heartfelt lyrics, “Courtesy of the Red, White, and Blue” is a reminder of the sacrifices made by those who defend our freedom.

“Red Solo Cup”: The Ultimate Party Anthem

Last but certainly not least, we have “Red Solo Cup,” Toby Keith’s ode to the iconic party accessory.

With its catchy melody and tongue-in-cheek lyrics, this song is guaranteed to be stuck in your head for days.

Whether you’re throwing a backyard barbecue or hitting the town with friends, “Red Solo Cup” is the perfect soundtrack for letting loose and having a good time.


In conclusion, Toby Keith’s biggest hits have left an indelible mark on the world of country music.

From the nostalgic charm of “Should’ve Been a Cowboy” to the raucous energy of “Red Solo Cup,” each song tells a story and evokes a feeling that resonates with fans around the world.

So, the next time you’re in need of a musical pick-me-up, just press play on one of Toby Keith’s greatest hits and let the good times roll!


1. What is Toby Keith’s most successful album?

  • Toby Keith’s most successful album to date is “Unleashed,” which includes hits like “Courtesy of the Red, White, and Blue” and “Beer for My Horses.”

2. Has Toby Keith won any awards for his music?

  • Yes, Toby Keith has won numerous awards throughout his career, including multiple Academy of Country Music Awards and Country Music Association Awards.

3. Does Toby Keith write all of his own songs?

  • While Toby Keith is known for writing many of his own songs, he also collaborates with other songwriters from time to time.

4. How many number one hits has Toby Keith had?

  • Toby Keith has had a total of 20 number one hits on the Billboard country charts throughout his career.

5. Is Toby Keith still actively making music and touring?

  • Yes, Toby Keith continues to release new music and tour regularly, delighting fans with his energetic performances and catchy tunes.

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