4 amazing Chris Stapleton award show performances are not hard to find. Chris is known for his incredible award-show performances. As we celebrate his birthday this week (4/15), we look at four of his very best award-show moments.

My History With Chris

I remember the first time I came face-to-face with Chris Stapleton. He was an unknown, and a PR office in Nashville had a bunch of us over for a visit to see this new “incredible talent.” They tell us that kind of thing a lot; every new artist is an “incredible talent.” But as I was standing and waiting for this new talent to arrive, a guy with a t-shirt, an open plaid shirt, and a beard started to chat me up and asked about where I was from. I was friendly and told him about my hometown, which he said he visited a lot, and remarked how clean the city was.

The guy then politely excused himself, strapped on a guitar, and started to play for us. I was astonished that the unassuming and kind guy I was talking to was Chris Stapleton. They weren’t kidding. It was immediately apparent that he was, in fact, an incredible talent.

It seemed like just months later, after his breakout CMA performance with Justin Timberlake in 2015, Chris was all anybody was talking about, and with good reason.

GRAMMY

Ten GRAMMY wins later, this guy can do no wrong when it comes to music and performance. He is now known for his amazing award show performances and that Super Bowl National Anthem performance in 2023 that had people talking about more than the actual game itself.

Chris Stapleton and producer Dave Cobb accept the Best Country Album award for Traveller onstage during The 58th GRAMMY Awards at Staples Center on February 15, 2016, in Los Angeles, California
Larry Busacca/Getty Images 

Higher

Stapleton told us of his latest album, Higher, when he released it in November, “One thing that’s probably notable about the record to me is it’s the first one that we’ve put out that doesn’t contain a cover, so there are no covers on this record. So, there’s definitely some exploration of the edges of what that is, and certainly some moments of stretching out vocally and trying to see what that is. There’s some different stuff on this record, and I think it’s really great.”

He added, “I think it’s something that people will enjoy. I think there’s something on it for everybody, which is kind of always my goal. If you’re a kind of a hardcore traditional country person, there’s a song on there for that somewhere. If you leaned into more of the R&B side of what we do, there’s stuff on there for that. If you like the rock side of things that we do, there’s stuff on there for that. And there’s some really great songs on here. I’m excited about the songs on this record.”

To celebrate the country superstar’s birthday this week, we look at four amazing awards show performances he has given in the last few years.

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  • "Tennessee Whiskey/Drink You Away" Medley with Justin Timberlake from the 2015 CMA Awards

    This performance was a lot of fans’ first exposure to Stapleton; it superchraged his career overnight. Timberlake performed with his friend because, at the time, he already knew how great Chris and his music were.

    We are grateful to Justin for sharing Stapleton with us. Ever since, we’ve loved him and looked forward to every award show performance from the country star.

  • "You'll Never Leave Harlan Alive" with Patty Loveless at the 2022 CMA Awards

    Such a powerful award show performance, and Stapleton never even recorded the song himself. The song has been recorded on albums by Patty Loveslle, Brad Paisley, Montgomery Gentry, and more.

    The song is about the life and hardships of coal miners in Kentucky, Stapleton’s native state. This performance garnered a standing ovation from the CMA Awards show crowd. The performance also reminds us why Loveless was inducted into the Country Music Hall of Fame.

  • "Cold" at the 2021 CMA Awards

    Chris sang this heartwrenching song solo at the 2021 CMA Awards and brought the crowd to tears with the tale of a heartbreak. The song was the second single from his fourth studio album, Starting Over. The lyrics to the chorus are: “Oh, why you got to be so cold? / Why you got to go and cut me like a knife / And put our love on ice? / Oh, girl, you know you left this hole / Right here in the middle of my soul / Oh, why you got to be so cold?”

    At the 64th Grammy Awards, the song won the award for Best Country Song.

  • "The Weight" Stapleton, Elton John Sheryl Crow, Brittany Howard Rock Hall 2023

    Chris starts this tribute to the song’s original writer, the Band’s Robbie Robertson, who passed away in August 2023. The song was released as the Band’s first single in 1968 and was the group’s debut album, Music from Big Pink.

    As per usual, Chris delivered this collaboration at the Rock Hall with grace and dignity.

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