Chris Stapleton Sings “Whenever You Come Around” in Front of Vince Gill and Brings the House Down

Some moments on stage don’t just entertain. They stop time. They remind you why certain artists aren’t just good, they’re built different.
That’s exactly what happened when Chris Stapleton took the stage during CMT Giants: Vince Gill and delivered a powerful, soul-soaked version of “Whenever You Come Around.” With Vince Gill sitting just a few feet away, Stapleton didn’t try to reinvent the wheel. He leaned in with quiet confidence, letting the song speak loud and clear.
Originally written by Vince Gill and Pete Wasner in 1994, the track was already one of the most beloved ballads in country music. But hearing Stapleton sing it — stripped down, nothing but vocals and an acoustic guitar — gave the song new weight. He didn’t push or showboat. He just let the emotion do the work.
Before singing, Stapleton took a moment to speak directly to Gill. He didn’t ramble. He just said what mattered.
“I moved here wanting to be you,” he told him. “You had the courage to encourage me… and it really made a difference. I love you from the bottom of my heart.”
It wasn’t just heartfelt. It was a rare moment of respect and gratitude between two generations of country greatness.