See Justin Timberlake, Chris Stapleton Reunite for 'Tennessee Whiskey'

Pop superstar and country singer join forces for three songs at Pilgrimage Festival outside Nashville

Justin Timberlake and Chris Stapleton sing "Tennessee Whiskey" at Pilgrimage Festival in Franklin, Tennessee.

When it comes to show-stopping charisma, Justin Timberlake and Chris Stapleton are poles apart in how they captivate. One is a quintessential pop star, hyping the crowd and working every inch of the stage with high notes, hot steps and a bottomless supply of sex appeal. The other is a compelling stoic who can plant himself at center stage and devastate an audience with his wrecking ball voice. And yet – as America learned in a now legendary 2015 CMA Awards performance that was a career-maker for Stapleton and a game-changer for country music – these polar opposite powerhouses have an inscrutable chemistry that bridges the gap between polished pop R&B and raw, uncluttered traditional country.

That chemistry was back on display for a capacity crowd of more than 25,000 Saturday night, when Stapleton made a lengthy guest appearance during Timberlake's headlining set at the Pilgrimage Music and Cultural Festival in Franklin, Tennessee, 20 miles south of Nashville.

"This man and this woman that I'm about to bring out have inspired me so much since I met them," Timberlake, who bought in as a producer of Pilgrimage last year, told delighted festivalgoers before introducing Stapleton and his wife and singing partner Morgane Stapleton to the stage over the slow-walking intro to "Tennessee Whiskey," the Dean Dillon- and Linda Hargrove-penned classic Timberlake and Stapleton performed at the CMAs, and which Stapleton cut on his 2015 debut Traveller. "Just when I thought I had the best beard onstage," Timberlake quipped before the pair, along with their respective backing bands, recreated the famed 2015 performance of the song in what was now their second time onstage together.

The compliments, and the Stapleton tunes, didn't end there.

"I figured Peter and Mary needed a Paul," Timberlake gushed, joking that he's long been stalking the Stapletons, before trading verses with them on an astounding take on the latter's reliably soul-shattering Traveller favorite "Fire Away."

By the time they were into "Sometimes I Cry" – the third and final song of the Stapleton mini-set – the pair was locked in a heated-but-friendly sing-off. You've got to give it up to anyone willing to go toe-to-toe with an effortlessly golden-voiced, Otis Redding-channeling wailer like Stapleton and risk being upstaged. But Timberlake is no stranger to that kind of confidence, which he'd spent the previous hour or so of the show proving by knocking high notes out of the park – or in this case, farm – on hits and fan-favorites like "Cry Me a River" and "Drink You Away."

Timberlake also proved he doesn't need much in the way of showbiz bells and whistles, turning in a unique, uncharacteristically stripped-down show that featured his shit-hot backing band, the Tennessee Kids, but was free of choreographed routines, wardrobe changes and glass-bottom floating stages. In fact, Timberlake, a native Memphian, who two years ago planted roots in Franklin-neighboring Middle Tennessee hideaway Leiper's Fork, gave repeated Volunteer State shout-outs, felt as much like his new stomping ground's most-celebrated townie, mastering ceremonies at an outsized backyard barbeque, as he did one of the world's most iconic pop stars.

"I think we should make a deal," Timberlake said, referring to his friendship and musical chemistry with Stapleton. "Every time either one of us plays Tennessee, the other one is there."