From the time he released his 1993 debut single “Should’ve Been a Cowboy,” Toby Keith ruled country music. His unabashed patriotism and wicked humor helped the “Big Dog Daddy” sell more than 40 million records across his three-decade career. Keith left a gaping hole in the industry when he died Feb. 5, 2024, at age 62 following a two-year battle with stomach cancer. On this day in 1999, we witnessed the birth of the Toby Keith we all came to know and love when he released his revenge anthem “How Do You Like Me Now?!”
Videos by American Songwriter
Perhaps even more iconic than the song itself is its music video, when Toby Keith’s narrator treats the girl who rejected him in high school to a midnight show on the hometown football field where he once “wrote your number on the 50-yard line.” We see Keith, all swagger and bluster, declare, I couldn’t make you love me but I always dreamed about livin’ in your radio / How do you like me now?
It’s brash. It’s boastful. And damn, is it a lot of fun. Who doesn’t love a good underdog story?
The second single and title track off his fifth studio album, “How Do You Like Me Now?!” spent five weeks atop the Billboard Hot Country Songs chart beginning in March 2000. At the end of the year, Billboard declared it the No. 1 country song of 2000.
[RELATED: These 4 Toby Keith Songs Prove He Really Did Have a Soft Side]
Is This Toby Keith Hit About Anyone in Particular?
While it’s tempting to project an entire sordid backstory onto the song, Toby Keith loved “How Do You Like Me Now?!” for its universality. “It can be about an old flame or a boss or a teacher—whatever it means to each individual,” he said of the track, which he co-wrote with songwriter Chuck Cannon. “It was a fun song to write.”
How Do You Like Me Now?! was Keith’s first album with the now-defunct DreamWorks Records, after his previous label, Mercury Records Nashville, rejected most of the songs on it.
“You should have seen the disgusted looks I got when I submitted that song,” he recalled. “Apparently, girls were the only ones allowed to say that, demeaning the fellas who’d done them wrong. People at the company kept saying, ‘What about the female audience? Having the girl in the song cry and you feeling good about it – well, you can’t do that.’ I told them, ‘That happens in real life. Somebody has to do it.’”
Turns out, women loved it.
Featured image by Ron Galella/Ron Galella Collection via Getty Images
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