How Chris Stapleton Made It Big (& What Justin Timberlake Had To Do With It)

Chris Stapleton is a household name among country fans now but had been in the business for many years before getting his big break. Before working as a solo artist, Stapleton was a member of the bluegrass group SteelDrivers. Eventually, he enjoyed immense success with three tracks topping Billboard's Hot Country Songs charts. 

In 2015, Stapleton released his solo debut "Traveller," which was initially well-received, but far from a commercial smash hit. "Well, I wanted to make a record that I thought my dad would have liked," the "Starting Over" singer said about the project while appearing on "60 Minutes" in 2015. Stapleton claimed no one held the alchemy for crafting a hit record. "And there are a lot of songwriters who will claim that they know ... I really just think those guys are full of s***," he said.

Stapleton was invited onto the "Late Show with David Letterman" to promote his album, as the show wrapped up its run. "I had a moment where I was at soundcheck, and I realized where I was standing — in the Ed Sullivan Theater. All that kind of stuff kind of hit me at once," he told Taste of Country in 2015. 

Despite the exposure, it was not until a legendary performance that the country artist's career was catapulted into stardom.

At the 2015 CMAs, Chris Stapleton's debut album "Traveller" earned him nominations for new artist, album of the year, and male vocalist, and he took home all three awards. Taking home the hardware was nice, but an unforgettable performance alongside Justin Timberlake made the night truly memorable. The duo teamed up to perform "Tennessee Whiskey" and Timberlake's "Drink You Away" in a surprise medley. "We talked two months ago, before I had built the show," the country star recalled to Billboard in 2015. "But I told [Timberlake] immediately I would block out eight minutes." Almost overnight, Stapleton's "Tennessee Whiskey" became a smash hit, and his career was never the same. "The impact of the CMA stuff, the performance on the show, the sales aftermath ... all that stuff seems very not real," he told GQ in 2016.

Stapleton teaming with Timberlake was not a manufactured affair. The pair had been looking for an excuse to collaborate for a while. "We've known each other for a few years now. When his wife was pregnant, we talked about some things about being a dad," Stapleton told Billboard. 

The NSYNC alum took to Instagram after the performance and mentioned knowing Stapleton, and his wife very well. "Sometimes you meet people and feel like you've known them your whole life," Timberlake wrote. That was not the duo's last time creating a hit.

In 2018, it was Chris Stapleton's turn to give the assist to Justin Timberlake. The country artist jumped on Timberlake's "Say Something" track which wound up being a hit single off Timberlake's "Man of the Woods" album. "We wrote the song almost a year ago, so a lot of weird things were happening, and they still are, in the world," Timberlake said in 2018 during a Beats 1 interview. The "SexyBack" singer was alluding to a 2016 incident when he was embroiled in online controversy after being accused of cultural appropriation. "It was the first song we wrote together," he said of the Stapleton collaboration.

Stapleton wrote the majority of the lyrics for the single. "Sometimes the greatest the way to say something is to say nothing at all / But I can't help myself, no I can't help myself, no, no," was the refrain. The country artist made a sizeable imprint on the whole album, as he also contributed to the songs "Morning Light" and "The Hard Stuff."

Over the years, the duo stayed in touch, and in 2022, they recreated some of the magic from the past. While performing in Los Angeles, Stapleton brought out Timberlake and they performed "Tennessee Whiskey" together. "I guarantee most of you know me because of this man," Stapleton said, as a nod to their 2015 showstopping performance at the CMAs.