Chris Stapleton and Justin Timberlake delivered an unforgettable performance during the 2015 CMA Awards, combining their powerful vocals on a medley of “Tennessee Whiskey” and “Drink You Away.” This performance marked a pivotal moment for Stapleton, who not only took home three prestigious awards that night but also solidified his status in the country music scene. Their duet was a standout moment, captivating audiences and showcasing the seamless blend of R&B and country influences that both artists embody​.

Timberlake’s introduction of Stapleton was filled with admiration, setting the stage for a performance that would resonate with fans long after the show concluded. Their rendition of “Tennessee Whiskey,” a classic originally performed by David Allan Coe and later popularized by George Jones, perfectly highlighted Stapleton’s soulful voice. The song’s rich instrumentation and emotional depth allowed both artists to shine, drawing the audience into the moment​.

Since that iconic night, Stapleton and Timberlake have reunited on stage multiple times, including performances at the Pilgrimage Music & Cultural Festival and a surprise collaboration during a concert at the Kia Forum in Los Angeles​. Each appearance further cements their musical chemistry, demonstrating Timberlake’s appreciation for country music and Stapleton’s versatility as an artist.

The performance not only contributed to Stapleton’s rise to fame but also emphasized Timberlake’s ability to cross genres and connect with country music. The duo’s collaboration is a testament to the power of music to bridge gaps between different styles and bring artists together, leaving a lasting impact on fans​.