Chris Stapleton: ‘A Really Fun Time’ Is What Makes a Great Collab

At the CMA Awards on Wednesday night (Nov. 10), four-time Male Vocalist trophy winner Chris Stapleton and first-time CMAs performer Jennifer Hudson brought a packed house to its feet with their performance.

Joined onstage by a dozen of world-class musicians, the vocal titans delivered a stratospheric and raucous rendition of “You Are My Sunshine.”

The duet was one of the highlights of the night, and for many in the audience, it called to mind another time when Stapleton was part of an unlikely CMA Awards team-up that led to one of the biggest moments of the show. That was in 2015, when the then-up-and-coming singer-songwriter joined Justin Timberlake onstage for a show-stealing performance that’s still talked about today.

Now, with another extraordinary CMAs collaboration under his belt, Stapleton shrugs when asked what his secret is for creating iconic awards show moments, saying he doesn’t typically realize in the moment that he’s making musical history.

“No is the answer to that — I don’t realize it,” he tells Taste of Country and other outlets backstage in the show’s virtual press room, “But I do realize that I’m having a really fun time, and that’s what music is for me.”

While you can never predict what shows are going to be the ones that are going to stand out the most, Stapleton continues, choosing the collaborations that are the most fun is usually a pretty safe bet.

“I always feel like if we’re having fun playing music, someone’s going to have fun listening to it or watching it,” he reasons. “If you’re thinking about something other than having fun and playing music for people who wanna hear it and also wanna have fun, then you’ve missed the mark.”

Stapleton also picked up four new trophies at the 2021 CMA Awards: His Starting Over record won Album of the Year, while the title track of that project earned him wins in the Song of the Year and Single of the Year categories. He also brought home the Male Vocalist of the Year title.

A consummate entertainer, Stapleton’s already figured out a way to use those four awards — and the many others he’s won — to bring enjoyment to his fans.

“We have a little VIP thing that you can go see out on the road. So we carry a lot of these kinds of things out on the road so people can see ’em, because they really belong to the fans,” the singer explains of how he’ll share he trophies with his biggest fans. “That’s how I feel about it, so I try to let them see them, hold some of these things, out on the road.”