Kris Kristofferson is an Outlaw Country icon. Country fans know that he wrote some of the most popular songs in the genre. Songs like “Help Me Make It Through the Night,” “Me and Bobby McGee,” and “Sunday Mornin’ Comin’ Down” all came from his pen. Additionally, he was one-fourth of the iconic supergroup The Highwaymen. However, there’s much more to Kristofferson’s career than that.
Throughout his career, Kristofferson released eighteen studio albums. He also released more than 30 singles. However, very few of those songs became hits for him as a performer. Only one—“Why Me”—went to No. 1 on the Billboard Hot Country Songs chart.
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[RELATED: 4 Songs You Didn’t Know Kris Kristofferson Wrote for Other Artists]
With that in mind, here are four deep cuts from Kristofferson’s deep catalog that all country fans should know.
“Gettin’ By, High and Strange”—Kris Kristofferson on Living a Wild Life
Kristofferson saw marginal success with his first two albums—Kristofferson and The Silver Tongued Devil And I. Then, he released his third album, Border Lord. It peaked at No. 6 on the Billboard Top Country Albums chart. However, critics gave it poor reviews, calling it rushed and sub-par when compared to his first two outings.
The album is packed with good songs. However, none of them are as fun as “Gettin’ High, By and Strange.”
“Shake Hands with the Devil”—A Wicked Love Song
Kris Kristofferson released Shake Hands with the Devil at an uncertain time in his life. As the seventies came to an end, he was seeing more success as an actor than a recording artist. At the same time, he was in the midst of divorcing Rita Coolidge. He seemingly shelved all of those things when he penned the album’s title track.
“Shake Hands with the Devil” is the kind of love song that a rough-around-the-edges outlaw could dedicate to the nice girl he wants to date. More than that, it’s a great song from yet another underappreciated album.
“Closer to the Bone”—Modern Kris Kristofferson
Kristofferson released Closer to the Bone in 2009, as he drew closer to retirement. Originally titled Starlight and Stone, the lauded songwriter said the album was “about making sense of life at the end of this game.” The title track embodies that spirit in the best possible way.
“Casey’s Last Ride”—Pure Poetry
Kris Kristofferson included “Casey’s Last Ride” on his 1970 debut album Kristofferson. The album contains career standouts like “Me and Bobby McGee,” “Sunday Mornin’ Comin’ Down,” and “Help Me Make It Through the Night.” As a result, this melancholy piece of poetry tends to get overlooked.
Casey is an everyman who is down on his luck. The listener doesn’t learn much about the man in the song other than that he moves listlessly through his day. There’s no big message or exciting twist at the end. Certainly, there is no punchline. However, the song highlights Kristofferson’s storytelling abilities.
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