As you likely already know, the country supergroup consisted 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 the biggest hits and most iconic songs.
Not only did they play Highwaymen hits, they also borrowed from each artist’s catalogue, playing songs together like Johnny’s “Ring of Fire” and Willie’s “Always On My Mind.” It was truly a one-of-a-kind concert, and sadly something we’ll never get to see again considering Johnny, Waylon and Kris have all since passed on. But luckily for all of us, those artists continue to live through the music they left behind.
And they captured the entire American Outlaws concert in high-quality video and clear-as-day audio, so we can always go back and relive the iconic moment whenever we want to.
Today, I want to highlight one of the standout performances from that night – in my humble opinion. I’m a little biased because Waylon Jennings’ “Are You Sure Hank Done It This Way” is one of my all-time favorite songs. Released in 1975 as a part of Waylon’s Dreaming My Dreams album, it’s considered one of the most successful and popular tracks in Jennings’ entire catalog. It was also adopted as the anthem of the outlaw movement… and it’s a shorter track that’s ideal if you need a song to sing for karaoke night (I know from experience).
As the Highwaymen did multiple times throughout that concert, whoever the song belonged to got to take the reigns when it came up in the setlist. So Waylon stepped into the spotlight with all of his best country music buddies backing him up, and he sang the famous lines (albeit a little modified) from the his 1975 hit:
“Somebody told me when I first got to Nashville
‘Hoss, you’ve finally got it made!
Old Hank made it here, we’re all sure that you will’
But I don’t think Hank done it this way,
Did ol’ Hank really do it this way?”
And man, there’s just something about seeing all of the country music legends not only sharing the stage together, but also grinning from ear to ear as they did so. It truly looked like Willie, Waylon, Johnny and Kris were having the times of their lives up on stage. Not to mention that they all appear to be cheering one another on… make sure to keep an eye out for Kristofferson looking like a full-on fanboy of Waylon’s once the song wraps up.
It obviously also melts your heart knowing that three of the four band members are no longer with us. That’s what makes looking back on some of these older performances so special. The Highwaymen left us country music fans with some incredible albums and stellar live performances. It’s up to us to keep them circulating, and one moment that’s definitely worth a revisit is this American Outlaws: Live at Nassau Coliseum performance.
Check it out:
