Introduction
Toby Keith’s “How Do You Like Me Now?!”, co-written with Chuck Cannon, was released on November 22, 1999 as the title track and second single from his fifth studio album of the same name . The single—originally nearly shelved by his label—became a defining moment in Keith’s career after he personally lobbied for it to be released .
Upon its release, the song soared to No. 1 on the Billboard Hot Country Songs chart for an impressive five weeks and also marked his first crossover into the Billboard Hot 100, reaching No. 31 . By the end of 2000, it stood as the No. 1 country song of the year, according to Billboard year-end rankings .
The track’s lyrics recount the story of someone once overlooked—perhaps by a love interest, a teacher, or a peer—who flips their narrative by rising to fame and asking, “How do you like me now?” This resonated widely, embodying a powerful message of vindication and perseverance . Keith himself said the song stemmed from his experiences of being doubted: “A lot of people become successful after they’ve been told they won’t ever be,” he explained .
Critically and culturally, the song solidified Keith’s reputation as a bold, unapologetic storyteller. The album also grabbed several ACM Awards, including Single of the Year in 2001, while Keith earned Album of the Year as both artist and producer .
More than 20 years later, “How Do You Like Me Now?!” remains one of his signature anthems, often lauded for its defiant spirit, catchy melody, and timeless relevance—not just in country music, but to anyone who’s ever overcome adversity .