After a string of singles that failed to crack the Top 40, Toby Keith returned to the forefront of country music in 1999 with 'How Do You Like Me Now?!,' the first single from his fifth studio album of the same name. Our No. 31 choice for the Top 100 Country Songs countdown rejuvenated country radio's interest in the Oklahoma native, giving Keith his first No. 1 in three years.

"A lot of people become successful after they've been told they won't ever be," Keith said of the tune's inspiration back in 2000. "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."

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Listen to 'How Do You Like Me Now?!' by Toby Keith