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Toby Keith Recalls Facing Early Rejection, Fighting for ‘How Do You Like Me Now?!’

Toby Keith early career
Kevork Djansezian, Getty Images for dcp

Toby Keith almost didn’t make it into country music. During his talk at the 2017 Country Radio Seminar, the Oklahoma native recounted his early days of trying to succeed in Nashville, and how he considered giving up before he even got a record deal, after one industry executive told him that his songs weren’t good enough.

“I had a meeting with Jimmy Bowen at Capitol. When I went in there and played, it was on a cassette, and he was just hitting fast forward. He’d play a verse and a chorus, and he’d hit fast forward,” Keith remembers. “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.’”

Thankfully, a friend believed in Keith — now a Songwriters Hall of Fame member — enough to give his music to producer and record label head Harold Shedd, who asked to meet the singer and hear his songs live. Shedd signed Keith to Mercury Records, but it took some time — and Keith ultimately announcing that he was going to “do his own thing” — before the now-star was comfortable with the music he was making.

“If you look at those first photo shoots, they had us in suits,” Keith shares. “Finally, I started dressing out of my closet and recording the songs I wanted to record … I put up with it for four years, and then I said, ‘I’m going to go down with my own ship. I can live if I go down with my ship. But if I’m not the captain and you guys take it down, I can’t sleep at night. So we’re going to do it this way, and if you don’t like it, then I don’t like you.’

“So then, I started saying, ‘These are the songs that I want to cut that you guys will never record,'” Keith continues. “I changed producers, and I went with James Stroud, and he just said, ‘You bring ‘em, I’ll cut ‘em.’ And so, we cut everything I wanted to record.”

See Toby Keith + More Stars Then and Now

When Mercury didn’t believe that the album Keith was recording contained a hit song, the artist explains that he convinced the label to drop him, bought the project off of them and went to DreamWorks. Keith’s first record on DreamWorks was How Do You Like Me Now?! — and its title track was a song that even Keith’s new label wasn’t keen on releasing as a single.

“Radio had gotten to where it was real female driven … They said, ‘This won’t work, telling a girl, ‘How do you like me now?’” Keith recalls. “And so the label wouldn’t put it out first.”

Instead, DreamWorks promoted “When Love Fades” as the record’s lead single, until Keith took matters into his own hands.

“I said, ‘What’s going to happen if this thing doesn’t hit?’ And they’re like, ‘Well, we don’t know. We’re going to go with this,'” Keith says. “We debuted, and we’re at 33 for three weeks in a row … So I just called 30 radio guys, and I said, ‘Go to “How Do You Like Me Now?!””

“How Do You Like Me Now?!” became one of the biggest hits of Keith’s career: It stayed at the top of the charts for five weeks, and its album earned an ACM for Album of the Year. How Do You Like Me Now?! is available for purchase at Amazon and iTunes.

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