On This Day: Toby Keith Scores No. 1 Hit with ‘How Do You Like Me Now?’ in 2000

by Katie Maloney
(Photo by M. Caulfield/WireImage)

Twenty-one years ago, Toby Keith asked us all, “How Do You Like Me Now?”

If there was an anthem for proving haters wrong, it would be Toby Keith’s “How Do You Like Me Now?” The song is about finding success despite people’s skepticism. During the song, Keith sings, “How do you like me now? Now that I’m on my way. Do you still think I’m crazy standing here today? I couldn’t make you love me but I always dreamed about living in your radio. How do like me now?”

Toby released “How Do You Like Me Now?” as the second single from his album of the same now. The song spent five weeks in the number one spot on the Billboard Hot Country Songs chart. It became Toby’s fourth number-one hit song. It also became his first crossover hit – the song also peaked at number 31 on the Billboard Hot 100 chart. Additionally, Toby Keith snagged an Academy of Country Music award nomination in 2001. He was nominated for Single of the Year and Song of the Year.

Toby Keith’s “How Do You Like Me Now?”

What’s the Story Behind Toby Keith’s Hit Song?

So what inspired Toby Keith to write “How Do You Like Me Now?” During an interview, Toby said that the song was inspired by one of his own catchphrases.

“Initially, I said, ‘Here’s my title: ‘You Never Loved Me Before, So How Do You Like Me Now?’ It’s one of my catch-phrases. A lot of people become successful after they’ve been told they won’t ever be, so people can relate to this,” said Toby. “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.”

Toby co-wrote the song with Chuck Cannon. Toby Keith said that after finally finishing the song with Chuck, he knew he had a hit song.

“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,” said Toby. “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.”