As rain poured down outside, within downtown Nashville’s Category 10 multi-level bar it was warm and cozy — and ultimately packed to the rafters — on day two of Billboard Country Live. Billed as On the Rise, Friday’s (June 6) lineup featured seven hot newcomers who, based on their infectious sets, all have promising futures.
Day two followed Thursday’s (June 5) Billboard Country Live Presented by Bud Light, which highlighted six acts, including Mitchell Tenpenny, Reyna Roberts, Alexandra Kay, Drew Baldridge, Max McNown and Ashley Cooke.
CMT host Carissa Culiner emceed both evenings, keeping things lively between sets, with assistance from DJ Grant Fisher.
Annie Bosko performs during Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenne.
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Annie Bosko
Bosko, whose new Stone Country Records album arrives in October, was the perfect opener to kick off the afternoon with her warm, welcoming presence and denim shorts and vest.
The California native opened with the spirited “California Cowgirl,” explaining “because I think no matter where you’re from, you’ve got a cowgirl inside,” before launching into her inspirational current single, “God Winks.” “I’ve hit low points in my life when I wanted to give up and I got a sign from God to keep going,” Bosko said, as fans held up their lighted cell phones, waving their arms in the air. She closed her short set with “(Country Girls) Who Runs the World,” an empowering twangy successor to Beyoncé’s “Run the World (Girls)” that saw her accompanying herself on harmonica.
Harper Grace performs at Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenn.
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Harper Grace
Sporting a T-shirt that read, “Country music makes you live longer,” the Curb Records artist opened with a sassy, thumping version of “Mr. Mystery” and followed up with the fiddle-laden “Take It Like a Truck,” which would fit right in on a Lainey Wilson album. Grace then went old school with a gorgeous version of the classic heartbreaker “Tennessee Waltz,” first made famous by Patti Page in 1950, before closing out with “IDK,” her current duet with Franklin Jonas, who, dressed in a dapper suit, joined her to the audience’s delight. The two roamed the stage as they sang the searching ballad about trying to find a love that has previously eluded them.
Graham Barham performs at Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenn.
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Graham Barham
Barham, backed with a full band, kicked the energy up with his blend of country, rock and trap beats on songs like the intoxicating “MIA” and the driving “Camo.” The Sony artist showed off his sense of humor as he introduced “Whiskey,” admonishing the audience to “please remember everything you see on screen isn’t necessarily true. With that being said, this is about me getting hammered.” He followed with a faithful version of Brooks & Dunn’s “Red Dirt Road,” before finishing strong with his boisterous hit, “Oil Money,” as accomplices shot fake money into the audience.
Cooper Alan performs at Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenn.
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Cooper Alan
Alan brought the party with him in a ridiculously high-energy, fun set, which started with the loping “To the Bar,” adding he used to play in the location before it became Combs’ Category 10. His cover of choice was a galloping version of Avicii/Aloe Blacc’s “Wake Me Up,” which he admitted he goofed up, but made up for it by inviting the audience to jump along with him in a unifying moment. He then launched into “the stupidest thing we’ve ever done,” his TikTok viral novelty hit, “Cold 45,” which was inspired by Afroman’s “Because I Got High.”
Alan and the audience caught their collective breaths when he turned serious, slowing it down and strapping on a guitar to play the sweet ballad “Take Forever (Hally’s Song),” which he wrote about his wife, whom he married in September 2023. But he finished by raising the roof again with “Plead the Fifth,” a hilarious ditty sung to the tune of “Auld Lang Syne,” with rapid-fire lyrics, from which he segued, appropriately enough, into John Michael Montgomery’s “Sold (The Grundy County Auction Incident)” and Eminem’s “Without Me.” Alan wasn’t on stage for a long time, but he was definitely there for a good time.
Timmy McKeever performs at Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenn.
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Timmy McKeever
There was cause for celebration for Big Loud artist Timmy McKeever, who had moved to Nashville exactly a year ago and showed why he’d already made great strides in that time. In a striking acoustic set with just him and his guitar, the 18-year-old deliberately slowed down the pace and showed off his sweet voice and fine writing skills with such tunes as the earnest, romantic “I’ve Known Better,” his first song to go viral on TikTok (“for the first two lines,” he joked) and the vulnerable “Bulletproof” (an original, not a cover of the recent Nate Smith hit). He then delivered a tasty cover of Megan Moroney’s “Tennessee Orange” — dubbed “Tennessee Orange (Breakup Version)” — that had not only a gender flip, but a twist, where he’s a Georgia boy in love with a girl who is now wearing Tennessee orange for her new beau, before going into a softer, less aggressive version of Toby Keith’s “Courtesy of the Red, White & Blue.”
He finished with three originals that showed off his promise as a budding talent, the yearning, infectious “Cravin’ You,” the upcoming single “Hold You to It,” and “Lightning Speed,” a song about losing yourself to the music industry.
Jake Worthington performs at Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenn.
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Jake Worthington
Armed with just an acoustic guitar, the 2014 The Voice contestant and Big Loud artist conjured up the ghosts of country legends like George Jones and Waylon Jennings with his twangy, authentic traditionalism and big voice.
Even breaking a guitar string early on (which he eventually was able to replace) didn’t slow down Worthington on songs like the irrepressible, upbeat “I’m the One” (the recorded version of which features Marty Stuart) and the aching “Hello S—ty Day,” which would have felt just right performed by Jones.
His 30-minute set was filled with such chestnuts, including the up-tempo, yet downtrodden “It Ain’t the Whiskey” and “Not Like I Used To,” before the Texan played “Ain’t Got You a Hold,” a western swing twirler that would have done George Strait proud. His cover of Merle Haggard’s “Half a Man” fit perfectly in his wheelhouse and was delivered with just the right amount of pathos.
Tayler Holder performs at Billboard Country Live On the Rise at Category 10 on June 6, 2025 in Nashville, Tenn.
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Tayler Holder
From the time he stepped on stage, Holder had the audience eating out of his hand. With more than five million Instagram followers, it felt like all the influencer-turned-country- singer’s fans were crammed into Category 10.
Holder prowled the stage as he launched in the hypnotic “Neon,” immediately hand-slapping with the front row with a bad-boy appeal that connected with the audience.
His set showed off his ease tackling various tempos and styles, including “Time in This Truck,” which conjured up a windows-down, wind-in-your-hair feel, as well as the slowed down breakup song “Someone You Knew,” followed by another breakup song he wrote about a four-year relationship that went south, “California Tennessee.” (Happy ending: There’s a new girlfriend in the picture.)
Holder, who moved to Nashville three years ago, and his band did a blazing mini-set of covers that opened and closed with a few bars of “Sweet Home Alabama” and a raucous “Freebird,” with a sweet version of One Direction’s “What Makes You Beautiful,” Florida Georgia Line’s “Cruise” and Teddy Swims’ “Lose Control” (delivered by Holder’s gruff-voiced guitarist) in between.
Holder than ended his set — and day two of Billboard Country Live — with a new song that has already garnered more than a million stream in a few days, the mid-tempo, propulsive “Ain’t You Leaving,” and “Dyin’ Flame,” which has more than 12 million streams. Holder penned the song with Barham. “We sent it to Morgan [Wallen] and [he] politely sent it right back to me,” Holder said. “I’m glad he did.”