In the annals of country music lore, few moments capture the raw camaraderie of legends like the 1991 interview with The Highwaymen—Johnny Cash, Kris Kristofferson, Waylon Jennings, and Willie Nelson—where Kristofferson unceremoniously dubbed Cash’s own “Big River” the greatest country song ever written, with the Man in Black sitting mere feet away. The exchange, resurfaced in a viral clip this week, has reignited nostalgia for the supergroup’s unbreakable bond, blending humor, humility, and high praise in a way that only these outlaws could pull off. As Cash’s 92nd birthday approaches in February, the story underscores the mutual respect that fueled their careers and cemented their place in music history.

The moment unfolded during a casual chat with New Zealand host Paul Holmes on his primetime show, filmed in Nashville and aired in 1991. The Highwaymen, formed in 1985 as a casual jam session that birthed three platinum albums, were at the peak of their collaborative fame. Holmes, ever the provocateur, posed a loaded question: “Who do you think is the best country singer of all time?” The room tensed with the weight of egos that could fill arenas, but the quartet handled it with the easy grace of men who’d shared stages, secrets, and suppers for years.

Willie Nelson kicked off with Hank Williams’ “I’m So Lonesome I Could Cry,” a nod to the hillbilly poet who shaped his outlaw ethos. Waylon Jennings picked “Dreaming My Dreams,” a Waylon staple penned by Allen Reynolds that mirrored his rebel heart. Cash, modest as ever, chose “I Love You Because,” the 1948 Leon Payne ballad popularized by Jim Reeves, emphasizing its emotional purity over flash. Then came Kristofferson, the Rhodes Scholar turned roughneck songwriter, who paused before delivering his zinger: “Maybe ‘Big River.’ I’ve often thought that that may be the best song, country or otherwise.”

The studio erupted in laughter—Jennings slapped his knee, Nelson chuckled deeply, and Cash, seated to Kristofferson’s right, broke into a wide grin, shaking his head in mock disbelief. “Big River,” released on Cash’s 1958 Sun Records debut Johnny Cash Sings the Songs That Made Him Famous, was his own creation, a rollicking tale of a lovesick drifter chasing a girl down the Mississippi. Penned in a Memphis motel room after a heartbreak, it became a signature hit, blending rockabilly bounce with Cash’s booming bass that mimicked the river’s flow. Kristofferson’s pick wasn’t flattery—it was a genuine salute from a peer who’d penned “Sunday Morning Coming Down” and “Help Me Make It Through the Night,” songs that Cash himself championed.

Kristofferson, 55 at the time, had every reason to toot his own horn. A former Army helicopter pilot turned Nashville janitor, he’d crashed a borrowed chopper on Cash’s lawn in 1969 to pitch “Sunday Morning Coming Down,” a gritty hangover anthem that Cash recorded and took to No. 1, launching Kristofferson’s career. Cash, ever the mentor, had already boosted him by including “The Last Thing on My Mind” on his 1967 album Everybody Loves a Nut. Their bond deepened in The Highwaymen, where Kristofferson’s poetic edge balanced Cash’s gravelly gravitas. “Kris was the intellectual firecracker,” Jennings later recalled in his 1996 autobiography. “He’d say something profound, and Johnny would just nod like it was gospel.”

The interview’s levity masked deeper ties. Cash and Kristofferson shared addictions—Cash to pills, Kristofferson to booze—and recoveries, with June Carter Cash playing a pivotal role in both. Kristofferson credited Cash for pulling him from obscurity, while Cash leaned on Kristofferson’s lyrics for emotional depth in later albums. Their Highwaymen tenure produced anthems like “Highwayman,” a 1985 No. 1 hit about reincarnation across eras, and fostered lifelong friendships. Even after Jennings’ 2002 death and Cash’s in 2003, Kristofferson and Nelson carried the torch, touring as a duo until Kristofferson’s 2020 retirement due to memory issues.

“Big River” itself is a cornerstone of Cash’s oeuvre. Clocking in at 1:58, it’s a whirlwind narrative: “Now I taught the weeping willow how to cry / And I showed the clouds how to cover up a clear blue sky.” Cash wrote it inspired by a Hank Williams lick and his own wanderlust, recording it with Luther Perkins’ twangy guitar and the Tennessee Two’s train-like rhythm. It peaked at No. 4 on Billboard’s country chart and became a live staple, often extended with Kristofferson-esque improv. Covers abound—Grateful Dead’s 1972 version, Johnny Paycheck’s 1973 take—but Cash’s remains definitive, earning a spot in the Grammy Hall of Fame in 2015.

The clip’s resurgence, shared by Whiskey Riff on October 16, 2025, has racked up 2.5 million views, with fans flooding comments: “Kris roasting Johnny live is peak Highwaymen energy” and “Proof true friends hype your own work.” It coincides with a Cash revival: The 2023 biopic The Man in Black on Paramount+ drew 15 million streams, and Kristofferson’s 2024 tribute album The Pilgrim Chapter 33 features Highwaymen rarities. Nelson, 92, continues touring, often dedicating “Big River” to Cash and Kristofferson.

This anecdote humanizes titans who reshaped country from Nashville’s polished polish to outlaw grit. Cash, with 71 albums and 14 No. 1s, and Kristofferson, with an Oscar for “For the Good Times” and a Kennedy Center Honor, weren’t rivals—they were brothers in black. As Kristofferson once said, “Johnny was the real deal.” In that interview, praising “Big River” wasn’t shade; it was scripture.