2 Songs Written by Kris Kristofferson, Released by Fellow Highwayman Waylon Jennings First

Nearly two decades before Waylon Jennings and Kris Kristofferson joined forces for their supergroup, the Highwaymen, in 1985, the former outlaw had already recorded several of his bandmate’s songs. Along with covering songs by mentor Harlan Howard, Johnny Cash, Roy Orbison, Merle Haggard, and Bob Dylan, among others, during the late 1960s, Jennings started tapping into some of Kristofferson’s lyrics from his 1971 album The Taker/Tulsa.

In the years that followed, Jennings also covered Kristofferson’s “To Beat the Devil” on his 1972 album Good Hearted Woman and “Me and Bobby McGee” a year later on Lonesome, On’ry and Mean.

During the early ’70s, there were two more songs written by Kristofferson that Jennings also recorded first.

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[RELATED: 3 Songs Kris Kristofferson Wrote for Some of the Women in His Life]

“The Taker” (1971)

Written by Kris Kristofferson and Shel Silverstein

Kristofferson’s “The Taker” became the title track of Waylon Jennings’ 1971 album The Taker/Tulsa and follows the story of a man who takes a woman for granted before leaving her.

He’s a charmer, he’ll charm her with money
And manners that I never learned
He’s a leader, he’ll lead her across
Pretty bridges he’s plannin’ to burn

He’s a talker, he’ll talk her right off of her feet
But he won’t talk for long
‘Cause he’s a doer, and he’ll do her the way
That I’d never, damned if he won’t do her wrong

At the time, the song was co-written with Shel Silverstein, who also co-wrote “Once More With Feeling” on Kristofferson’s 1979 album Shake Hands with the Devil. Jennings also covered Kristofferson’s “Casey’s Last Ride” and “Sunday Morning Comin’ Down” on The Taker/Tulsa.

Kristofferson later recorded “The Taker” on his second album, The Silver Tongued Devil and I, in 1972, produced by his “Me and Bobby McGee” co-writer, longtime producer and Monument Records founder Fred Foster, who also worked closely with Roy Orbison—who would later record Kristofferson’s “Something They Can’t Take Away” (see below)—and worked with Willie Nelson and Dolly Parton early on in their careers.

“Loving Her Was Easier (Than Anything I’ll Ever Do)” (1971)

Written by Kris Kristofferson

In 1971, Kristofferson scored another hit, “Loving Her Was Easier (Than Anything I’ll Ever Do Again),” from his second album, The Silver Tongued Devil and I. The single peaked at No. 26 on the Billboard Hot 100 and No. 4 on the Adult Contemporary chart. Months before Kristofferson released his version, Jennings was the first to release the song in February 1971 on The Taker/Tulsa. Bobby Bare and Ray Price also released versions of the song before Kristofferson released his own in July that year.

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
Turning on the world, the way she smiles upon my soul as I lay dying
Healing with the colors of the sunshine and the shadow of her eyes

Waking in the morning to the feeling of her fingers on my skin
Wiping out the traces of the people and the places that i’ve been
Teaching me that yesterday was something that I never thought of trying
Talking about tomorrow and the money, love, and time we’d have to spend
Loving her was easier than anything I’ll ever do again

Coming close together with a feeling that I’ve never known before, in my time
She ain’t afraid to be a woman or afraid to be a friend
I don’t know the answer to the easy way she opens every door in my mind
Dreaming was as easy as believing it was never gonna end
Loving her was easier than anything I’ll ever do again

“I went to Los Angeles and cut Kris Kristofferson’s ‘Lovin’ Her Was Easier’ with Ricky Nelson’s band,” recalled Jennings in his 1996 memoir Waylon. “At the time, he had a good bunch of guys with him, including Sonny Curtis. It was a great record, up-tempo with a good guitar riff. They [RCA] wouldn’t release it because it was recorded in L.A. They didn’t want to set a precedent. They didn’t know who I was or what I was about, and I tried my best to keep ’em in the dark.”

Photo: Ron Galella, Ltd./Ron Galella Collection via Getty Images