Most country artists dream of a career like Toby Keith had, and one he enjoyed for more than 30 years. Keith was still making music when he was diagnosed with stomach cancer, passing away on February 5, 2024.
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Beginning in 1993, Keith had hit after hit at radio. While no one could have predicted the career he would have, these four early hits hinted that Toby Keith would become a country music superstar.
“Should’ve Been A Cowboy”
“Should’ve Been A Cowboy” is Keith’s first single and his first No. 1 hit. Written by Keith for his eponymous debut record, “Should’ve Been A Cowboy” is inspired by a true story.
Keith was on a hunting trip with some friends when one of the guys got turned down by a girl at a dance club.
“A guy said to another guy, ‘In all honesty, you should’ve been a cowboy,’ when a girl didn’t dance with him in his hunting clothes,” Keith recalls to The Oklahoman. “And I thought, ‘Man, that sounds like a song idea,’ and it was all over me.”
“Should’ve Been A Cowboy” says, “I should’ve been a cowboy / I should’ve learned to rope and ride / Wearin’ my six-shooter, ridin’ my pony on a cattle drive / Stealin’ the young girls’ hearts / Just like Gene and Roy / Singin’ those campfire songs / Whoa, I should’ve been a cowboy.”
“How Do You Like Me Now?!”
Out in 1999 as the title track of Keith’s sixth studio album, the singer wrote the bold tune with Chuck Cannon. The song is about overcoming other people’s expectations, delivered as only Keith can.
“How Do You Like Me Now?!” says, “How do you like me now? / Now that I’m on my way / Do you still think I’m crazy standing here today? / I couldn’t make you love me, but I always dreamed about livin’ in your radio / How do you like me now?“
One of Keith’s most successful songs, “How Do You Like Me Now?!” stayed at the top of the charts for five weeks.
“Who’s That Man”
The debut single from Keith’s 1994 sophomore Boomtown album, Keith is the sole writer of “Who’s That Man”. The sad song is about regret over a marriage ending.
“Who’s That Man” says, “That’s my house and that’s my car / That’s my dog in my backyard / There’s the window to the room / Where she lays her pretty head / I planted that tree out by the fence / Not long after we moved in / There’s my kids and that’s my wife / But who’s that man runnin’ my life?“
“I’m So Happy I Can’t Stop Crying” With Sting
Not many country artists got to sing with a pop artist of Sting’s caliber, but Keith isn’t most artists. The country music icon released “I’m So Happy I Can’t Stop Crying” in 1997. Written by Sting, he first recorded the song on his Mercury Falling project. Later, Keith includes the duet version on his Dream Walkin’ record.
“I’m So Happy I Can’t Stop Crying” says, “I saw a friend of mine / He said, ‘I was worried about you / I heard she had another man / I wondered how you felt about it’ / I’m so happy that I can’t stop crying / I’m so happy I’m laughing through my tears.”
Photo by Ron Galella/Ron Galella Collection via Getty Images
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