Musician Justin Timberlake (L) performs onstage with Singer-songwriter Chris Stapleton (R)performs onstage at the 49th annual CMA Awards at the Bridgestone Arena on November 4, 2015 in Nashville, Tennessee.
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6 Times Justin Timberlake Went Country, From 'Tennessee Whiskey' to 'Love's Got a Hold on You'

Justin Timberlake is a man of many talents — he's a singer, songwriter, actor and record producer. The former NSYNC member is one of the world's best-selling musicians, selling over 88 million records thus far. He's also a recipient of several accolades and awards including 10 Grammy Awards, four Primetime Emmy Awards, nine Billboard Music Awards and three Brit Awards. He even received the Contemporary Icon Award from the Songwriters Hall of Fame.

Starting off on The All-New Mickey Mouse Club, the singer has explored several genres throughout his career, including pop, rock, R&B, and yes, even country. Most notably, he's worked with one of the greatest country singers out there, Chris Stapleton, collaborating with him for his song, "Say Something."

Here are some of the best country moments Timberlake has been a part of.

Country From The Start

Before the singer blew up and became an international star, he began his career on Star Search at just 11 years old. Timberlake, who was going by his first and middle name at the time, decided to compete in the singing competition as Justin Randall singing an ode to Alan Jackson. Dressed like a cowboy, Timberlake predicted his future.

Honestly, even at a young age in 1992, you can tell he was born to be a star. Just listen to the audience clapping along and cheering young Timberlake on. Unfortunately, he lost by .75 stars, but hey, that didn't stop him!

Justin Timberlake and Reba Hit The Stage

Talk about an iconic performance! Fast forward a few years, Timberlake was part of McEntire's duet album in 2007. Fun fact, he actually wrote the song, which initially had made the country artist a little worried since he was known for his raunchy singles such as "SexyBack."

"I didn't know if it was going to be SexyBack 2, 3 or 4," McEntire stated. "I was really nervous. I didn't know how I was going to say no to a song I didn't like if Justin had written it."

Reba: Duets was McEntire's twenty-seventh studio album, produced by McEntire, Dann Huff, Tony Brown and Justin Timberlake. Other singers featured on the album include LeAnn Rimes, Kelly Clarkson, Carole King, Trisha Yearwood, Faith Hill, Kenny Chesney and more.

"Say Something"

Timberlake and Chris Stapelton pretty much broke the internet (and radios), after releasing "Say Something." The song was released on January 25, 2018 as the third single from Timberlake's fifth studio album, Man of the Woods. Becoming a fan favorite, the song debuted at No. 9 on the US Billboard Hot 100 — the pop singer's 19th top 10 single as a solo artist and Stapelton's first. The song received a nomination at the 61st Annual Grammy Awards for Best Pop/Duo Group Performance.

Speaking about the process of creating the song, Stapelton stated, "I really just went out to Los Angeles to write songs with him. It's a very fluid process with him, there's a lot going on. That was one of those things where there wasn't necessarily a plan. He was like 'All right, you hop in there and take a verse,' and I'm like, 'You want me to do what?' ... It came out great. I had a blast with him, he's a great creative force and one of those guys that if you get a chance to work with him, you should."

The official music video for the song is epic and definitely one of my favorites.

Chris Stapleton and Justin Timberlake Reunite for "Tennessee Whiskey"

Teaming up one more time (which probably won't be the last) the duo teamed up again this year for a live performance after Stapleton welcomed Timberlake for a duet of "Tennessee Whiskey" during his concert in Los Angeles on June 10, 2022. "I guarantee that most of you probably know me because of this man I'm about to bring onstage," the country singer said when introducing Timberlake. "He's one of the greatest musical artists that has ever lived."

Timberlake quickly walked out on stage, hugged Morgane Stapleton, took a few bows and performed "Tennessee Whiskey," which appeared in Stapelton's 2015 album, Traveller. The duo had previously performed the song during a medley at the CMA Awards in 2015. "Tennessee Whiskey '' spent six weeks total on the Billboard Hot 100 in 2015, peaking at No. 20 in November of that year.

Hank Williams Jr.'s Stamp of Approval

Jason Kempin/Getty Images for Country Music Hall of Fame and Museum

Okay, so this one isn't necessarily Timberlake performing, but it's a pretty big deal. Back in 2012, the pop singer was seen backstage in Mississippi with his best friend and business partner Trace Ayala, hanging out with the legend himself, Hank Williams Jr. The country artist was doing a concert in Southaven, which Timberlake and his now-wife Jessica Biel attended.

"What a great guy! Justin is a friend of my rebel son Kid Rock," Williams said at that time. "He sure is a good country boy. We talked about girls, guitars, turkey hunting, going on cruises and how much we hate them, even though Bobby (Kid Rock) is on one right now and loving it, ugh! Hell, Justin and I even talked about recording a blues song sometime.

Garth Brooks and Timberlake Have "Friends in Low Places"

Back in 2014, Timberlake played in Nashville, where he decided to cover Brooke's "Friends in Low Places." As the crowd cheered, Timberlake quickly stopped his tracks, saying that something was off. "I mean if you're going to do this — Garth?," he said while the crowd yelled in excitement! Brooks walked on stage and performed the duet with Timberlake, who crashed to the floor after they finished, clearly overwhelmed by the experience. Can you blame him? It's Garth Brooks!

READ MORE: 5 Times Katy Perry Proved Her Love of Country Music, From Dolly Tributes to Country Co-Writes