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.
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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.
