Why Toby Keith Never Went Back to the Woodshed

“I Knew I Was Right,” He Tells Country Radio Seminar Crowd

The only reason Toby Keith bothered coming to Nashville was because he knew a guy who had a nephew who knew a guy.

When he spoke at the Country Radio Seminar in Nashville on Friday (Feb. 24), Keith told the story of his first attempts at getting a record deal in the early ’90s.

And it goes like this:

The owner of a bar where Keith played in Oklahoma City had a nephew who was a musician and a songwriter with a few friends in the business. So he set up a meeting for Keith, who went in and played some of his songs on a cassette.

“I went in, and the guy would play a verse and a chorus then hit fast forward,” Keith recalled.

“He goes, ‘Well, that’s all good and fine, and you sing good, but you need to go back to the woodshed and work on your songwriting. These songs aren’t gonna cut it.'”

“I was like, ‘Cool. I’ll go back to the bar and not worry about this no more,'” he said.

He wasn’t disappointed, he said, because he still had the chance to keep throwing a few of his own songs in between the Garth Brooks, George Strait, Willie Nelson and Merle Haggard covers in his set. (Even though some bar owners would tell him to “just play the jukebox.”)

“You finally find guys who will let you play your own music, and then you come out here to Nashville, and you just get kicked in the teeth,” he said.

But around that same time, one of Keith’s friends and fans took the same cassette that the first guy didn’t think would “cut it” and gave it to her friend Harold Shedd, a music executive and producer already known for his success with Alabama and Reba McEntire, among others.

“Harold called me and said, ‘Would you play these songs live for me?’ I played them, and he signed me right then,” Keith said of his first deal with Mercury Records.

“So I never did go back to the bars in Oklahoma. I knew I was right. Those were the songs I thought they were. I’d just had the wrong guy,” he said.

The songs Keith played for both industry bigshots were “Should’ve Been a Cowboy,” “He Ain’t Worth Missing,” “Wish I Didn’t Know Now,” “Does That Blue Moon Ever Shine on You,” “Valentine” and “Close but No Guitar.” Four of them ended up at the top of the country charts.

There’s no word on where that first Nashville executive ended up. I’m guessing maybe he’s back in the woodshed.

Alison makes her living loving country music. She's based in Chicago, but she's always leaving her heart in Nashville.