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15 Years Ago: Toby Keith Hits No. 1 With ‘How Do You Like Me Now?!’

Toby Keith How Do You Like Ne Now cover art
DreamWorks Nashville

Fifteen years ago today (March 18, 2000), Toby Keith said plenty to his critics and fans when his latest single “How Do You Like Me Now?!” soared to the top of the charts.

The song, which was the title track of his fifth studio album, was Keith’s response to people who said that he would never make it in the music business.

“A lot of people become successful after they’ve been told they won’t ever be,” Keith says of the inspiration for the tune, which he wrote with Chuck Cannon. “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.”

“How Do You Like Me Now?!” stayed at No. 1 for five weeks and was the No. 1 song on Billboard’s year-end Country Songs chart for 2000. The album also earned Keith two ACM Awards; he received Album of the Year as both artist and producer.

Still, in spite of the success of the song and the album, which landed in the Top 10 and sold more than one million copies, the Oklahoma native struggled to find the creative freedom to release the kind of music he wanted to make. After his label, DreamWorks, shut down in 2005, Keith started his own label, Show Dog Nashville, later partnering with Universal South Records to create Show Dog-Universal in 2009.

“I won’t be that guy that I was running from,” Keith says of the reason for creating his own label. “I’m not going to go in and be the big fat guy with the cigar with his feet kicked up. I’m an artist, and I’ve got a big career that I need to go work. All I’m doing is changing the place that my music sells. You’ll still go to the same stores. It will still be distributed by the same people. It will just be created and come through a different set of books. That’s the only thing that changes.”

The move clearly worked for him. Since he created his own label, Keith has had eight Top 5 albums, and more than 20 Top 40 singles.

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