Introduction
On November 2, 2016, at the CMA Awards’ 50th Anniversary held in Nashville’s Bridgestone Arena, Alan Jackson and George Strait joined forces for a soulful duet of Jackson’s “Remember When” and Strait’s “Troubadour,” creating one of the most talked-about moments of the night. For four unforgettable minutes, these two country legends set aside competition to celebrate their shared roots and lifelong friendship, delivering a performance that fans still replay today.
“Remember When” was penned and recorded by Alan Jackson as the second single from his 2003 compilation Greatest Hits Volume II, ultimately reaching No. 1 on Billboard’s Hot Country Songs chart and cementing its status as a modern classic. George Strait’s “Troubadour,” released in 2008 as the title track of his album Troubadour, reflects on a lifetime of music-filled adventures, earning praise for its warm nostalgia and Strait’s timeless delivery. Both songs are deeply personal: Jackson’s ode to love and memory and Strait’s tribute to the wandering musician’s spirit.
Alan Jackson opened their duet with a delicate, almost conversational delivery of “Remember When,” his voice carrying the weight of decades-long marriage vows as a montage of CMA acceptance speeches played behind him. When George Strait stepped in for “Troubadour,” the stage lights softened around him, spotlighting the genuine emotion in his weathered baritone as he sang about life’s journey. The seamless transition between the two songs—minus any elaborate staging or pyrotechnics—underscored that raw talent and heartfelt storytelling remain country music’s greatest spectacles.
What made this duet so powerful was its simplicity and sincerity. Rather than vying for showmanship, Jackson and Strait leaned into each other’s legacies, trading knowing glances and smiles as if sharing private jokes onstage. Fans watching at home felt as though they’d been invited into an intimate living room concert, complete with two friends reminiscing about the highs and lows of life in song. The audience response—a standing ovation that lasted well into the next act—proved that when legends unite, their combined history becomes a gift to every listener in the room.
Have you ever experienced a live moment that gave you chills? What duet—country or otherwise—stands out in your memory? Share your favorite live performance in the comments and let’s keep celebrating the magic of music together.