In this song, Toby Keith recalls his unrequited attraction with a female valedictorian back in his high school years who never paid any attention to him. He wonders if she remembers him now that he's famous.

Keith co-wrote this with Chuck Cannon. He explained in publicity materials: "Chuck and I have had so much success together. We started writing this song right after we finished another one. We got through the first verse, and I was just blown away by it.

Chuck thought it was kinda okay, but when you've just got a little piece of a song, it sometimes doesn't stick out when you've got a finished product layin' there. I kept telling him this was gonna be a big song if we could just nail it.

It took us about six months to get back to it after that. But we finally did get back together - and nailed it."

This spent five weeks at #1 on the Country chart and, according to Billboard, it was the biggest selling country song of 2000.

This was the lead song on the album, but when Keith gave it to his record company (Mercury) they informed him that most of the tracks on the CD, for lack of a better word, "sucked."

He asked if he could have the songs back and they told him he could buy them back, which he did.

He then walked across the street (to DreamWorks) and sold the album for twice as much.

He fondly recalled being able to sing "How Do You Like Me Now?!" at the CMA Awards, all the while thinking of his former company.

Keith said in 2000 regarding the inspiration for the tune: "A lot of people become successful after they've been told they won't ever be. So people can relate to this. It can be about an old flame or a boss or a teacher - whatever it means to each individual. It was a fun song to write."