Kris Kristofferson: 3 Outsiders Wax Poetic About Their Favorite Songs to Celebrate Kris’ 85th Birthday

by Jim Casey
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Kris Kristofferson is the baddest man to ever add “country music artist” to his resume. Let that sink in for a second, because it’s not hyperbole. The man was a Golden Gloves boxer, Rhodes Scholar at Oxford University, a U.S. Army Ranger, and a commercial helicopter pilot before making the full-time move to country music.

Simply put, Kris is a Renaissance Man. With his poetic approach to crafting songs like “Why Me,” “Me and Bobby McGee,” “For the Good Times,” and more, he became one of the most revered songwriters in the history of country music. While his contributions as a tunesmith outweigh his personal successes as a singer, the man had stage presence, too. Of course, Kris also made the transition to the silver screen by starring in dozens and dozens of films.

In honor of Kris Kristofferson’s 85th birthday on June 22, 2021, we tasked Outsider‘s Wes Blankenship, Clayton Edwards, and Jim Casey to wax poetic about their favorite songs from Kris’ catalog.

‘Loving Her Was Easier (Than Anything I’ll Ever Do Again)’

Wes Blankenship, Outsider content producer

I enjoy “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” for two reasons:

  • It’s going to make Jim Casey sweat out the character limit of the Tweet to this link.
  • Kristofferson’s opening lyrics make me envision a scene that would make for a sweet airbrushed T-shirt.

“I’ve seen the morning burning golden on the mountains in the skies / Aching with the feeling of the freedom of an eagle when she flies.”

Some of the lyrics about his love with this woman are a little too obscure for me to fully pick up what Kris is putting down, but I don’t mind. Spoiler alert: Obviously it didn’t work out in the long run.

“Dreaming was as easy as believing it was never gonna end / Loving her was easier than anything I’ll ever do again.”

Doesn’t matter though. Just the thought of this . . . uh . . . relationship? Makes Kris think about an eagle flying above mountains that are burning golden by the sun. Wow. I hope he got an airbrushed T-shirt to commemorate it. Good luck with the Tweet, Jim.

‘Gettin’ By, High, and Strange’

Clayton Edwards, Outsider staff writer

Country music is full of songs about traveling. However, this one stands out among the crowd. It’s an honest and gritty tune that just happens to be a real toe-tapper. At the same time, it’s all about coping with hard times in life by traveling, taking any drug that comes along, and connecting with an unfamiliar woman.

Coming from just about anyone else, it would be a song full of sorrow and regret. Kris, though, celebrates his hard and fast living.

For me, it’s the duality and honesty of the song that does it. Kris really strikes a balance between dark times and good times. More importantly, he was openly sharing how he was living his life. At the end of the day, this one is hard to beat. 

‘Sunday Mornin’ Comin’ Down’

Jim Casey, Outsider senior editor

“Sunday Mornin’ Comin’ Down” reads like it could have been written by a Romantic Poet. It’s a complete literary assault on my fives senses. I can taste the “beer for breakfast,” smell the “fryin’ chicken,” hear the “lonely bell,” see the “cleanest dirty shirt” and touch the “Sunday mornin’ sidewalk.”

It’s pure poetry. What happened next is legendary.

Determined to get his demo of “Sunday Mornin’ Comin’ Down” in the hands of his idol Johnny Cash, Kris Kristofferson landed a helicopter in Johnny’s front yard in 1969. That’s moxie. Of course, Cash capitulated and his rendition of the song reached No. 1 in 1970.

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