Toby Keith Fantasizes Aloud in “How Do You Like Me Now?!”

On November 22, 1999, Toby Keith released “How Do You Like Me Now?!” as the second single from his fifth studio album. The song swiftly soared high, ranking No. 1 on Billboard’s Hot Country Songs chart – where it spent five weeks atop. It also marked his first crossover success on the Billboard Hot 100, peaking at No. 31.

Today, it remains one of the most popular hits by Toby Keith. In fact, after his passing on February 5, 2024, “How Do You Like Me Now?!” re-entered Billboard’s Hot Country Songs chart at No. 23.

The Meaning Behind The Song 

Written by Toby Keith and renowned country music songwriter Chuck Cannon, “How Do You Like Me Now?!” tells the story of a man remembering his high school years being the “crazy one” trying to get the attention of the perfect girl. However, she consistently ignored him. She even made fun of him when he took off to Tennessee.

Fast forward to many years later, he finds himself wondering what she thinks of him now that he has become a country star. 

On his website in 2000, Keith talked about what inspired the song. Keith knew many individuals achieved success despite being told they never would, making this song relatable for many. “It can be about an old flame or a boss or a teacher – whatever it means to each individual,” he said, adding that he had fun writing the tune.

Well, it’s time to crank up the volume and dive into the world of Toby Keith’s “How Do You Like Me Now?!” It’s a musical journey that might just strike a chord with your soul. Play the video below, and let the lyrics weave their magic!