Before he ever had a record deal, Toby Keith sat in a Nashville office and watched Capitol Records boss Jimmy Bowen fast-forward through his demo cassette. Years later, a song about proving the doubters wrong would become the biggest country single of 2000. That song was “How Do You Like Me Now?!”, and the story of how it reached the radio fits its title almost perfectly.
A Demo Tape and a Trip Back to the Woodshed
In his early Nashville days, Toby Keith was a young Oklahoman with a big voice and a stack of songs. When he played his demo for Jimmy Bowen at Capitol, he did not get the answer he hoped for. Bowen said he could sing, but told him to “go back to the woodshed” and work on his songwriting.
Toby Keith later admitted he came close to giving up. Then a friend, who has since been inducted into the Songwriters Hall of Fame, passed his music to producer and label head Harold Shedd. Harold Shedd asked to hear the songs live, and soon Toby Keith had a deal with Mercury Records.
Suits, Polish and a Growing Frustration
The early years at Mercury brought success, but they never felt quite right to Toby Keith. He remembered the label putting him in suits for his first photo shoots and trying to smooth out his rough edges. After about four years, he told the label he was going to do his own thing and record the songs he believed in.
He began working with producer James Stroud, who agreed to cut everything Toby Keith wanted. One of those songs, written with Chuck Cannon, was a cocky, grinning anthem built on one of Toby Keith’s own catchphrases.
The Story Inside the Song
“How Do You Like Me Now?!” follows a narrator who was overlooked by his high school crush. She never gave him a second look back then. Years later, he has made it big, his voice is on her radio, and he can’t resist asking what she thinks of him now.
Toby Keith never wanted fans to pin one backstory on it. He said the song could be about an old flame, a boss or a teacher, whatever it meant to each listener. “It was a fun song to write,” he said.
Two Labels, Zero Believers
Mercury did not hear a hit on the album. So Toby Keith did something bold: he got the label to release him, bought the project back and took it to DreamWorks Records.
Even at his new home, the song made people nervous. Executives argued that country radio was driven by female listeners, and that a song taunting a woman with “How do you like me now?” would never work. DreamWorks released a different single, “When Love Fades,” as the first single instead.
The Phone Calls That Changed Everything
“When Love Fades” debuted at No. 33 and stayed stuck there for three weeks. Toby Keith had seen enough. He told the label they were not giving him the chance to “fire my biggest missile.”
Then he took matters into his own hands and called about 30 radio programmers himself, asking them to switch to the title track. Within five days, the label pulled “When Love Fades” and released “How Do You Like Me Now?!” in its place.
“So they pulled the single in five days… and my career exploded.” — Toby Keith
From Doubted to No. 1
The single was released in November 1999. On April 5, 2000, it reached No. 1 on the U.S. country chart. By the end of the year, Billboard had named it the No. 1 country single of 2000. The album went platinum and won Album of the Year at the Academy of Country Music Awards.
More importantly, the song changed who Toby Keith was in the public eye. The polished young singer in a suit was gone. In his place was the brash, funny and unapologetic Toby Keith that fans would follow for the next two decades.
Why the Song Still Matters
It is hard to miss the irony. A song about being underestimated was itself underestimated, first by one label and then by another. Toby Keith answered the doubters the same way his narrator did: by ending up on the radio, louder than ever.
Anyone who has ever been told “no” by a crush, a boss or an entire industry can hear a bit of their own story in it. That is why, more than 25 years later, “How Do You Like Me Now?!” still sounds less like a boast and more like a promise kept.
Frequently Asked Questions
Who wrote “How Do You Like Me Now?!”?
Toby Keith wrote the song with Chuck Cannon.
Why didn’t the label want to release it?
DreamWorks executives worried that a song taunting a woman would not work on female-driven country radio, so they released “When Love Fades” first.
How successful was the song?
It reached No. 1 on the U.S. country chart on April 5, 2000, and Billboard named it the top country single of the year.