Who Will Follow in Kris Kristofferson’s Footsteps?

Still Selling Out Shows at 80

Editor’s note: Kris Kristofferson will perform on CMT’s all-star concert special Outlaw: Celebrating the Music of Waylon Jennings, airing April 7 at 10 p.m. ET/PT.

Can you picture Luke Bryan on stage in 2056? Is it possible that Miranda Lambert will sell out shows in 2063? Could Sam Hunt still be performing in 2064?

After seeing Kris Kristofferson on Wednesday night (March 22) at a sold-out show at Chicago’s City Winery, I think so. I think anything is possible.

Kristofferson will be 81 this summer, which is a fact that is at once remarkable and irrelevant.

Because while a singer may age, great songs rarely do.

That’s the power of music. The good stuff can be so timeless.

Evidence of that came from Kristofferson’s set list full of tunes off his first two albums from 1970 and 1971. So he was singing songs that were almost 50 years old to some fans who were half that old.

He opened his one-man show, with a harmonica and a guitar, with “Shipwrecked in the Eighties” then quickly moved into “Darby’s Castle,” off his debut album.

And then without any long-winded introduction or humble brags, Kristofferson started to sing one of his most well-known tunes, “Me and Bobby McGee.”

The song was made most famous by Janis Joplin, but the oft-covered song’s fame grew steadily as country artists like Johnny Cash, Waylon Jennings, Loretta Lynn, Dolly Parton and LeAnn Rimes recorded their own versions.

After having a little harmonica trouble on the song, Kristofferson told the crowd, “That was horrible.”

While his playing and singing were far from flawless, the roughly 300 fans packed tight into the intimate room seemed more interested in his self-deprecating remarks than the in some kind of unattainable perfection.

The singer/songwriter/actor’s 90-minute set included “Here Comes That Rainbow Again,” “Best of all Possible Worlds,” “Nobody Wins,” “Broken Freedom Song,” “Sunday Mornin’ Comin’ Down,” “Why Me,” “The Pilgrim: Chapter 33,” “Please Don’t Tell Me How the Story Ends” and more.

When it came time for “Help Me Make It Through The Night,” Kristofferson tossed a one-word joke into the lyrics, singing, “Help me make it through tonight.”

One of the newest songs in his set was “Feeling Mortal,” from his 2013 album of the same name. And nestled in the chorus was a lyric that felt like Kristofferson could’ve written it just for the night.

I thank my lucky stars
From here to eternity
For the artist that you are
And the man you made of me

Alison makes her living loving country music. She's based in Chicago, but she's always leaving her heart in Nashville.