When two country legends with a combined 180 million records sold and 35 CMA Awards join forces, it’s bound to be a moment for the ages. That’s exactly what happened when George Strait and Alan Jackson, both three-time CMA Entertainers of the Year, teamed up for a historic performance at the 50th CMA Awards in Nashville on November 2, 2016. The crowd was in for an unforgettable treat.

Alan Jackson kicked off with his iconic 2003 hit “Remember When,” setting the stage for a moment of pure country magic. But the real surprise came when George Strait joined him, taking the spotlight to perform “Troubadour,” the title track of his 2008 album.

Their voices intertwined effortlessly, creating a powerful harmony that filled the room with emotion. It wasn’t just a performance—it was a heartfelt tribute to the roots of country music, where every word spoke of life’s highs and lows. In those moments, the stage was transformed into something special, proving once again why these two legends will always hold a place in country music’s heart.

Before the CMA Awards, Jackson shared that the CMAs were one of the most memorable moments of his career. “I knew the others a little bit, and there are several different shows, even the Grammys, you know. Everyone wants to put that at the top, and that’s cool but to me, I was a country singer. I wanted the Country Music Association awards,” he said.

“It’s very cool, especially at my age. Been through so much, been on so many shows, won every award there is, but being able to come back and be a part of it and celebrate this big year, that’s an honor.”