These 4 Toby Keith Songs Prove He Really Did Have a Soft Side

Toby Keith is known in country music for brash songs like “How Do You Like Me Now?!”, “I Wanna Talk About Me”, “Courtesy of the Red, White and Blue (The Angry American)”, and more. But in spite of his sometimes tough exterior, there was another, more gentle side of the Country Music Hall of Fame member.

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We found four songs that show that Toby Keith did indeed have a soft side.

“Don’t Let The Old Man In”

Don’t Let The Old Man In” came out in 2018 as part of his Greatest Hits: The Show Dog Years record. Written solely by Keith, the song was inspired by a conversation Keith had with Clint Eastwood. The actor was 88 years old while starring in the movie The Mule. Keith asked Eastwood how he kept working at his age, with his response inspiring the song.

“He said, ‘I just get up every morning and go out. And I don’t let the old man in,’” Keith tells Billboard. “And I thought, ‘I’m writing that.’”

Many moons I have lived / My body’s weathered and worn / Ask yourself how would you be / If you didn’t know the day you were born,” Keith sings. “Try to love on your wife / And stay close to your friends / Toast each sundown with wine / Don’t let the old man in.”

Eastwood liked the song so much, he included it in The Mule. Keith singing the song is also his last performance on TV. Keith performed the song at the 2023 People’s Choice Country Awards. He passed away from stomach cancer on February 5, 2024.

“My List”

Toby Keith wrote “My List” with Rand Bishop. The song came out as a single in 2002, from Keith’s Pull My Chain project. The song comes between “I Wanna Talk About Me” and “Courtesy of the Red, White and Blue (The Angry American)”, a surprising show of sincerity between the two bold tunes.

“My List” says, “I won’t break my back for a million bucks / I can’t take to my grave / So why put off for tomorrow / What I could get done today / Like go for a walk, say a little prayer / Take a deep breath of mountain air / Put on my glove and play some catch / It’s time that I make time for that / Wade the shore, cast a line / Look up an old lost friend of mine / Sit on the porch and give my girl a kiss / Start livin’, that’s the next thing on my list.”

“Love Me If You Can”

Keith doesn’t release a lot of tender, even vulnerable songs. But one that stands out is “Love Me If You Can,” one of the few songs Keith released that he didn’t write. Penned instead by Chris Wallen and Craig Wiseman, and released in 2007, the song gives a glimpse of Keith that he doesn’t often show.

I’m a man of my convictions / Call me wrong, call me right,” Keith sings. “But I bring my better angels to every fight / You may not like where I’m going / But you sure know where I stand / Hate me if you want to / Love me if you can.”

“Does That Blue Moon Ever Shine On You”

Keith shows a rare glimpse of regret in “Does That Blue Moon Ever Shine On You”. Written solely by Keith and released in 1996, Keith articulates the feelings of lost love. The lyrics clearly depict the angst of living with choices made, even if he wishes he could do it over again.

In “Does That Blue Moon Ever Shine On You,” the song begins with, “Day by day / We let love just walk away / And I’ll be the first to say / I was glad to see it go / And day by day / Ever since you went away / I find that I’m still missing you / And I just got to know / Does that blue moon ever shine on you.”

Photo by John Shearer/Getty Images for ACM

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