I’ve said it before and I’ll say it again, country music peaked with The Highwaymen.
Of course, they’re the country supergroup consisting of the genres most well-known outlaws, including Waylon Jennings, Willie Nelson, Johnny Cash and Kris Kristofferson.
And back in 1990, they held a special concert called American Outlaws: Live at Nassau Coliseum, where they joined forces to sing some of their biggest hits and most iconic songs.
From Johnny’s “Ring of Fire,” Willie’s “Always On My Mind,” Waylon’s “Are You Sure Hank Done It This Way,” and Kris’ “Help Me Make It Through The Night,” it was surely a helluva a show and something we’ll unfortunately never get to witness again, seeing as half of the band in Johnny and Waylon have since passed on.
But the performance of “Help Me Make It Through The Night” in particular was something special.
I’ve always had a special place in my heart for that song, and those four teaming up together to play it as a group is next level. They also gave it a bit more of an upbeat production and used some more electric guitar, and it just works.
A solo write by Kris, the track was included on his 1970 album Kristofferson, and has been covered by countless other artists since then like Willie Nelson, Gladys Knight & the Pips and Tyler Childers and Morgan Wade.
The track peaked at #1 on the U.S. Billboard Hot Country Songs chart in 1971.
Funny enough, Kris first got the inspiration from the song after reading an old Esquire interview with the late Frank Sinatra, where he was asked what he believed in and replied:
“Booze, broads, or a bible… whatever helps me make it through the night.”
And one of the greatest country songs of that decade, and possibly of all-time, was born… quite a story.
What I would give to go back and witness these four on stage together, though.
The charm and charisma in this single four-minute video is unbelievable:
“Help Me Make It Through The Night”