VIDEO: Chris Stapleton Returns to the Stern Show

Country star talks Super Bowl Performance, hanging with Willie Nelson, and his favorite collaborations

September 25, 2024

On Nov. 3, 2015, Chris Stapleton was a 37-year-old country singer who had just released his debut album a few months earlier. When he took the stage at the Country Music Awards the next night with pop superstar Justin Timberlake, his entire world changed.

“It’s such a great moment — the two of you guys performing together was certainly something I wouldn’t even think would occur,” Howard admitted to Stapleton, who made his return to the Stern Show Wednesday morning.

“Me neither,” the country star said with a laugh.

Stapleton had actually met Timberlake through a mutual friend and even discussed making an album together, but it was his wife Morgane who suggested he ask the former NSYNC star to perform with him at the CMAs. “Call him right now,” he remembered her insisting.

As an observer, Howard pointed out the electric performance the duo gave on their cover of David Allan Coe’s “Tennessee Whiskey.” “The two of you guys are up there and you’re lighting the whole room up,” he marveled.

Stapleton saw immediate payoff from the appearance. “After that night, [my shows] all sold out instantly and it was a different ball game,” he recalled before adding it introduced him to new fans, like producer Pharrell Williams. “There’s a picture somewhere of me and Pharrell and Timberlake on a bus, and I’m sure I look like I don’t know what’s happening.”

“I like to say, ‘Maybe we built the fire, but he threw the match on it,’” Stapleton added of Timberlake and their CMA duet. “That will always have a special place in my heart, and he will too.”