Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

Justin Timberlake and Chris Stapleton Sings a ‘Tennessee Whiskey/Drink You Away’ Medley during the CMA 2015

Justin Timberlake and Chris Stapleton Sings a ‘Tennessee Whiskey/Drink You Away’ Medley during the CMA 2015
by
  • Riley is a Senior Country Music Journalist for Country Thang Daily, known for her engaging storytelling and insightful coverage of the genre.
  • Before joining Country Thang Daily, Riley developed her expertise at Billboard and People magazine, focusing on feature stories and music reviews.
  • Riley has a Bachelor of Arts in Journalism from Belmont University, with a minor in Cultural Studies.

November 4, 2015 went down as the day when Chris Stapleton hit the charts as the No. 1 trending search term on Google and for a good reason. 

Before his stint on the 2015 CMA awards, even his top fans wouldn’t have thought that he would smash hits outside of country music.

However, this grizzled country songwriter teamed up with a clean-cut pop favorite. Together with Justin Timberlake, they stole the show at the 49th annual CMA Awards.

RELATED: When Garth Brooks Surprised Justin Timberlake For A “Friends in Low Places” Duet

Singing a two punch performance of Timberlake’s “Drink You Away” and Stapleton’s “Tennessee Whiskey,” this duo dazzled the audience, a performance that catapulted Stapleton to his current stadium-rocking star status. 

Chris Stapleton’s new fans were quick to wonder how the two-song medley came to be. The pair reportedly got together after Stapleton performed at Timberlake’s private event. The “Like I Love You” singer soon enough backed the industry’s relatively new name by singing at the said awards ceremony. 

Timberlake’s falsetto highlighted the highest notes of the song in Stapleton’s ‘Traveller,’ which also won Album of the Year. The medley took the fans to church as the band mesmerized them into reveling from start to finish. Fans came home wondering who sang with Timberlake with such power.

Proving his spicy singing prowess, this Kentucky-born voice became a beloved favorite soon after that night. Given the classic performance he gave to all spectators, Stapleton proved he only needed a little nudge by a friend. 

Stapleton’s iconic status today was a revelation into the mainstream music industry five years ago. Since then, the “Starting Over” singer wows his fans from all walks of life, both long-time country music buffs and new ones.

ICYMI, here’s the ‘Tennessee Whiskey/Drink You Away’ Medley:

Latest Stories

Jelly Roll performing in pouring rain on stage with intense passion, singing into microphone under dramatic lights, symbolizing redemption and faith journey in country music.

Jelly Roll Gets Honest About Faith, Forgiveness, and the Two Values He Says the World Needs Most

When Jelly Roll talks about his faith, you stop and listen because it does not sound like a sermon. It sounds like the truth. The “Son of a Sinner” singer ...

Kelly Clarkson delivers a powerful soulful performance of "No One Else Like Me" by The Red Clay Strays on The Kelly Clarkson Show.

Kelly Clarkson Puts Her Whole Soul Into Red Clay Strays Cover and Proves Nobody Can Out-Sing Her

Kelly Clarkson just took a Red Clay Strays song to church and back again, and fans are still picking their jaws up off the floor. It all went down during ...

Country icon Dwight Yoakam sings into microphone under stage lights in cowboy hat and denim, hosting a star-studded benefit "Rockin' for the Kids" at The Roxy on January 28, 2026, to support Children's Hospital Los Angeles with special guests including Charley Crockett, Marcus King, and Lukas Nelson.

Dwight Yoakam to Host Star-Studded Benefit for Children’s Hospital Los Angeles at The Roxy

Country legend Dwight Yoakam is trading the honky-tonk for heartfelt giving with a guitar in hand and a cause close to home. Just ahead of Grammy week, Dwight Yoakam is ...

Country star Megan Moroney sings passionately on stage in short denim dress and boots beside Riley Green strumming guitar in Nebraska cap, fueling rumors her upcoming track "Wish I Didn't" is a sharp breakup anthem directed at Riley Green with hidden clues.

Are Megan Moroney’s New Songs Taking Aim at Riley Green? Fans Think the Clues Add Up

Megan Moroney did not name Riley Green, but her lyrics sure sound like she circled his name in red ink. If you have been anywhere near country TikTok, Instagram comments, ...

Kelly Clarkson shares a rare family update on how her children River and Remington are coping after their father Brandon Blackstock's death, emphasizing snuggles and special bedtime moments that bring joy amid grief in 2026.

Kelly Clarkson Shares a Rare Update on How Her Kids Are Coping After Their Dad’s Death

Even through heartbreak, Kelly Clarkson is doing what strong mamas do best by putting her kids first. Kelly Clarkson may be a powerhouse on stage, but behind closed doors, she ...

Duck Dynasty star Mary Kate Robertson stands on the beach at sunset in a flowy white dress, proudly showing her growing bump with John Luke and their kids, revealing the exciting arrival of twin baby girls.

“Duck Dynasty” Star Mary Kate Robertson Shares Sweet Bump Update as She Awaits Twin Baby Girls

There is just something about the Robertson clan that makes you feel like family, and now it is about to get even bigger with two tiny, pink-bootied blessings. “Duck Dynasty” ...

Lainey Wilson, Reba McEntire, Miley Cyrus, Queen Latifah, and Dolly Parton unite for a powerful 2026 reimagining of "Light of a Clear Blue Morning," blending country legacy with soulful vocals, hope, strength, and unity in this star-studded collaboration.

Lainey Wilson Teams Up With Reba, Miley and Queen Latifah to Reimagine a Beloved Dolly Parton Song

When Dolly Parton joins forces with Lainey Wilson, Miley Cyrus, Reba McEntire, and Queen Latifah, you know something legendary is about to happen. Dolly Parton has never been one to ...

Wynonna Judd with long red hair and black sparkling outfit shares a heartfelt moment onstage with Bob Weir in dark coat and gray cowboy hat, as she honors his support after Naomi Judd's passing, calling him family in her emotional 2026 tribute following his death.

Wynonna Judd Remembers Bob Weir and the Incredible Thing He Did After Naomi Passed

Wynonna Judd just shared a powerful story about Bob Weir that proves real friendships in country music run deeper than the stage. As the music world mourns the death of ...

Bob Weir performs an intimate acoustic cover of "Mamas Don't Let Your Babies Grow Up to Be Cowboys" in a cozy home setting, strumming guitar in dark shirt while seated on a stool, delivering a soulful farewell that resonates deeply after his passing in 2026.

Bob Weir’s Final Country Cover “Mamas Don’t Let Your Babies Grow Up to Be Cowboys” Hits Different Now That He’s Gone

Bob Weir may be gone, but the soul he poured into his final country cover still echoes like a prayer. His soulful rendition of “Mamas Don’t Let Your Babies Grow ...

Chris Stapleton performs "Tennessee Whiskey" on stage in cowboy hat and dark jacket with guitar, as the song becomes the first country track to earn RIAA double diamond status with over 20 million units sold in 2026.

Chris Stapleton’s “Tennessee Whiskey” Becomes the First Country Song to Go Double Diamond

The smoothest pour in country music just became the strongest shot on the charts. Chris Stapleton‘s soul-drenched version of “Tennessee Whiskey” has officially become the first country song in history ...