Introduction
Released on November 22, 1999, “How Do You Like Me Now?!”, co-written by Toby Keith and Chuck Cannon, served as the breakout single and title track from Keith’s fifth studio album and first with DreamWorks Nashville—following his departure from Mercury Records . Initially dismissed by Mercury and early DreamWorks executives, Keith fought to release the song after “When Love Fades” underperformed—and it paid off spectacularly
The single became Keith’s first Billboard Hot Country Songs No. 1, holding the top spot for five weeks from March to April 2000, and earning No. 31 on the all-genre Billboard Hot 100—marking his first crossover pop success . It was also named the No. 1 country song of 2000 on Billboard’s Year-End chart .
Lyrically, the song channels themes of vindication and nostalgia. Its narrator recalls a high-school crush who once overlooked him, and now, as a successful musician, taunts, “How do you like me now?!” . Toby Keith has said the song reflects his own fight to prove himself after industry doubts, making it deeply personal
Critics praised the track’s feisty attitude and relatable story. Billboard’s Deborah Evans Price described it as “a great little tune about the underdog fulfilling his dreams…feisty” . Its success propelled the How Do You Like Me Now?! album to platinum status and earned Keith both Album of the Year and Top Male Vocalist at the 2001 ACM Awards