26 Years Ago Today, Toby Keith Hit No. 1 With This Signature Song That Proved His Label Wrong

Toby Keith introduced himself to the country music world with his chart-topping 1993 debut single “Should’ve Been a Cowboy”. From that point on, he did things his way. And he certainly reaped the rewards, racking up 20 No. 1 hits before his death in 2024 from stomach cancer. On this day (April 5) in 2000, the “Big Dog Daddy” was at No. 1 on the U.S. country chart with “How Do You Like Me Now?!” Ironically, his label had cautioned him against releasing the song at all.

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One of Toby Keith’s signature songs, “How Do You Like Me Now?!” is pure swagger. Speaking to a former love interest who shunned him in high school, the narrator gleefully rubs in his newfound success. I couldn’t make you love me but I always dreamed about livin’ in your radio / How do you like me now?

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♬ She’s Amazing – NURUL FARAHTASHA BINTI MOHHIDIN

“It can be about an old flame or a boss or a teacher—whatever it means to each individual,” Keith said. “It was a fun song to write.”

Toby Keith Had to Fight For This Song

In many ways, Toby Keith’s journey to recording “How Do You Like Me Now?!” mirrors that of the song’s narrator. In 2017, the future 14-time ACM Award winner recalled a meeting with a Capitol Records executive from his early days in Nashville.

“We got done, and he goes, ‘Well, that’s all good and fine. You sing good, but you need to go back to the woodshed and work on your songwriting. These songs aren’t going to cut it.’,” Keith said.

Eventually, he signed with Mercury Records. However, the Oklahoma native wasn’t comfortable with the label’s attempts to burnish his lyrics and image. In 1998, he finally walked away from Mercury after four albums, signing with DreamWorks instead.

[RELATED: 4 Early Toby Keith Hits That Hinted at His Superstar Career]

Released in November 1999, Keith’s sixth studio album How Do You Like Me Now?! underperformed at first, along with its lead single, “When Love Fades”. The country music hitmaker asked to withdraw “When Love Fades” as a single in favor of “How Do You Like Me Now?!” Despite misgivings from his label, Keith got his way.

“I said, ‘Man, you guys aren’t giving me the chance to fire my biggest missile,’” the singer told Billboard. “So they pulled the single in five days, put out ‘How Do You Like Me Now?!’” and my career exploded.”

Featured image by Brett Coomer/Houston Chronicle