The Bizarre Birthday Party That Led to Chris Stapleton and Justin Timberlake's Iconic CMA Awards Performance

When thinking of the most memorable moments in country music of the past decade or so, it's hard to look past Chris Stapleton and Justin Timberlake's unforgettable medley of ‘Tennessee Whiskey’ and ‘Drink You Away’ at the 2015 CMA Awards.

A genre-blurring link-up that ultimately launched Stapleton as one of the defining voices of the next ten years, and set the Kentucky native's version of ‘Tennessee Whiskey’ on the path to becoming the first country song in history to go Double-Diamond.

Although arriving as a bolt from the blue - and paving the way for their much-loved 2018 collaboration, ‘Say Something’ - Stapleton and Timberlake had already established a blossoming friendship that pre-dated their momentous CMA Awards set.

During his new appearance on Dax Shepard's Armchair Expert podcast, Stapleton recalls the unexpected invitation that initially put things in motion for the 2015 CMA link-up.

“[Justin] saw me on a YouTube video...”, he explains, “The first time I actually met him, it was his birthday, and his wife [Jessica Biel] called and said, ‘Hey, it's hard for me to find experiences that my husband hasn't had. Would you fly to Montana and play for his birthday party?’ I'm like, ‘Wow’. All of a sudden, I'm the experience”.

Stapleton then fast-forwards to how the intimate performance went, “We were there for like a day, and my wife [Morgane] is with me. We're like, ‘What are we doing here?’”

He expands, “So it's time to go do the party, and we get on this horse-drawn Santa Claus sleigh. We go up a mountain, and I'm thinking, ‘There's grizzly bears up here...’ And we go to this cabin with no electricity...We go in, there's one guy cooking on like an 1800s stove...The room not much bigger than where we're sitting right now, and just a small table. Like, what is happening? I felt like I was getting punked”.

Stapleton recounts the moment Timberlake walked in, “He finally shows up, and it's him, his best friend and a couple [of others], maybe his cousin or something. It was like six, seven people”, before taking the stage, “I play a little bit of music...and then he's like, ‘Hey, man, sit down’. So I wound up just sitting down, and we hung out that night and got somewhat friendly. Then we went back to his house, and...we definitely had some whiskey and had some Pappy [Reserve] that night”.

Stapleton playfully reflects, “There was a cake there, and I went to eat a piece. I cut a piece of this cake because I'd had a few whiskeys. [Someone] was like, ‘What are you doing cutting this cake?’ I looked...and Alicia Keys had sent him the cake. And he's like, ‘No man, it's cool, eat the cake’. That was kind of it. And we kind of knew each other from then on. And we had talked a little about...music, and we talked about doing things together. You know, we went out to dinner a few times”.

That paved the way for Stapleton to call Timberlake - at Morgane's encouragement - when the opportunity arose to deliver his first performance at the 2015 CMA Awards.

Immediately after Stapleton raised the prospect, Timberlake was on-board, with the duo then holding a meeting with the CMA producers. Stapleton laughs as he conveys how Timberlake ended up asking for eight and a half minutes for their performance - an “eternity” in TV time - but because of his star-power, the producers agreed.

And the rest, as they say, is history. Stapleton and Timberlake tore up the stage with their spellbinding performance, and it has since become a touchstone for the kind of headline-grabbing, cross-genre collaborations the CMAs have gravitated towards in the years since. We're hoping that, one day, Stapleton and Timberlake will run it back and serve us up a long-awaited sequel to ‘Say Something’, as well as hitting the stage once again for another catalogue-spanning medley...

Watch Dax Shepard and Monica Padman's full interview with Chris Stapleton on Armchair Expert below:

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