Six years later, Timberlake and Stapleton’s duet of “Tennessee Whiskey/Drink You Away” remains iconic.

The performance at the 2015 CMA Awards was a powerful demonstration of how music can bridge different genres and bring together artists with distinct styles. Chris Stapleton’s raw, emotive country voice complemented Justin Timberlake’s smooth, modern pop and R&B sound, creating a memorable and unique musical experience. The synergy between the two artists not only showcased their individual talents but also highlighted their ability to harmonize despite their different musical backgrounds.

Stapleton’s career has been marked by a series of collaborations that reflect his versatility and influence within the industry. Beyond his notable performance with Timberlake, Stapleton has worked with a range of artists, spanning various genres. His collaboration with Ed Sheeran on “Blow” exemplifies his ability to blend his country roots with rock and pop elements, creating a high-energy track that contrasts with his usual style but still showcases his vocal prowess.

Stapleton’s work with P!nk on “Love Me Anyway” is another example of his adaptability. This duet merges Stapleton’s country sound with P!nk’s pop and rock influences, resulting in a powerful ballad that highlights both artists’ strengths. The song’s emotional depth and lyrical content resonate with listeners, reflecting Stapleton’s ability to connect with diverse audiences through different musical styles.

In addition to these collaborations, Stapleton has also joined forces with Mike Campbell and The Dirty Knobs, contributing to their album Wreckless Abandon. This partnership highlights Stapleton’s flexibility and willingness to explore different musical landscapes, including rock.

Stapleton’s performances with Brandi Carlile also underscore his collaborative spirit. Their live performances often feature a blend of their unique styles, creating a dynamic and engaging musical experience. Carlile’s folk and Americana influences complement Stapleton’s country sound, resulting in performances that celebrate their shared love for authentic, heartfelt music.

Through these collaborations, Stapleton has demonstrated his ability to transcend genre boundaries and work with a diverse array of artists. His career is marked by a series of successful partnerships that highlight his versatility and reinforce his position as a significant figure in contemporary music. These collaborations not only enhance his own musical repertoire but also contribute to the broader musical landscape, showcasing the power of artistic synergy.