Kris Kristofferson's 10 Best Songs: Critic's Picks

Kris Kristofferson, 2017
Rick Diamond/Getty Images for Skyville

Kris Kristofferson performs onstage during Skyville Live Presents a Tribute to Jerry Lee Lewis on Aug. 24, 2017 in Nashville, Tenn. 

There are few entertainers who have left such an imprint on this world as Kris Kristofferson. Whether it be as a songwriter, a recording artist, or as an actor, he has scaled the highest plateaus of the industry – earning a spot in the Country Music Hall of Fame in the process.

In taking a look at the musical legacy of Kristofferson, this list is going to look a little bit different than the others we have featured as of late. There are five of his greatest performances as an artist himself, as well as five of the top Kris Kristofferson songs as recorded by other artists. Both reveal a legacy that is very much unlike any in the business – past or present.

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As a recording artist

5. Kris Kristofferson -"The Silver Tongued Devil And I"

The title track from his 1971 album, this song takes place in a bar with a man trying to pick up a woman and watching her waltz off in the arms of someone else. But, he surmises that the two are not that different in their personalities. The mystery of the song is whether he’s sorry or not for his actions. Forty-seven years later, we’re still not sure!


4. Kris Kristofferson - "When I Loved Her"

This emotional performance was one of many Kristofferson compositions that were also recorded by Ray Price. Understandably, his ragged vocal style was a lot different than Price’s, but this performance remains very much etched in fans’ minds – regardless of who was singing the lyrics of heartbreak. As it turned out, this song falls in the list of Kris’s contributions as an artist because there was that other song that Price recorded. Yep, you know that one!


3. Kris Kristofferson - "To Beat The Devil"

Another track from Kristofferson, this might very well be one of the most realistic instances of a number about the art of songwritng. As a new writer to town in the 1960s, the Texas native seen it all – and it shows in each and every line here.


2. Kris Kristofferson - "Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)"

Though the song became a No. 2 hit for Tompall and The Glaser Brothers in the early 1980s, the definitive version of this Kris Kristofferson song remains with the songwriter.


1. Kris Kristofferson -"Why Me"

His range as a vocalist might not be the greatest. Any musical expert will tell you that. But, what sets Kristofferson apart from the pack as a performer has nothing to do with a pristine vocal approach. In his shining moment as a performer, this number one Country hit from 1973 shines because of his plain-spoken take on the song. Simply put, it works because this song of gratefulness showcases a man who is as rough around the edges vocally as the lyrics of this timeless Kris Kristofferson song which features backing vocals from Rita Coolidge (his wife at the time) and a pre-stardom Larry Gatlin.


As a songwriter

5. Faron Young -"Your Time’s A’ Comin"

One of the most underrated songs in his catalog was this number that Faron Young took to the top-five in 1969. The humorous take on a man who stole a woman from someone else – who finds out that turnabout is only fair – was one of the earliest hits for Kristofferson as a tunesmith.


4. Kris Kristofferson - "Me and Bobby McGee"

Kris was inspired to pen this song – made into an American classic by Janis Joplin – because of calling Fred Foster at Monument. One day, Foster told him that he was only calling to talk to his secretary, who had a similar name – Bobby McKee. Roger Miller had the first hit on the track, and Kristofferson wasn’t even aware of Joplin’s version until the week of her death.


3. Kris Kristofferson - "Help Me Make It Through The Night"

Perhaps the most sexual song of its’ time, this Kris Kristofferson song became a classic recording for Sammi Smith. The million-selling seductive performance earned Smith a Grammy, a cross-over hit, and an eternal spot in the imagination of male Country fans everywhere.


2. Kris Kristofferson - "Sunday Mornin’ Comin’ Down"

As iconic as Johnny Cash’s 1970 version was, it wasn’t the first time up the charts. Ray Stevens took the song to No. 55 on the Country Singles chart in 1969, but it was “The Man In Black” who made it a worldwide hit. It also landed the singer in hot water with ABC brass who had asked him not to say Kristofferson’s line “Wishin’ I Was Stoned” during his performance of the song on his weekly TV series. When the camera rolled, Cash took the defiant stance of being a songwriters’ kind of artist – and sang it the way it was written, making a lifelong fan of Kristofferson in the process.


1. Kris Kristofferson - "For The Good Times"  

Never before – nor after – has a song about “one last time for old times’ sake” sounded as tender and romantic as Ray Price’s 1970 recording of the song that stands tall as not just one of the greatest Kris Kristofferson song moments of all time – but a highlight of Country Music history. A dramatic statement, for sure, but take a listen – and tell us we’re wrong!