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Bailey Zimmerman’s Heartfelt Country Closes Railbird Festival 2025 Day 1 with a Bang

By Larry Philpot on June 17, 2025

The Kentucky night was electric on May 31, 2025, when Bailey Zimmerman headlined the Elkhorn Stage at Railbird Festival. His 8:15 p.m. set was a high-octane blend of country heart and rock energy, lighting up Lexington’s Red Mile. Consequently, the crowd, packed shoulder-to-shoulder, sang every word of his hits. For an hour, Zimmerman, a small-town Illinois kid, poured his soul out, capping Day 1 with raw emotion.

His performance was a rollercoaster of anthems and ballads. For instance, he opened with “Fall in Love,” its driving beat igniting cheers. Meanwhile, his gravelly voice carried pain and passion, connecting instantly. His band—polished yet gritty—kept the energy soaring, with Jake Shirley’s guitar riffs cutting through. Moreover, “Rock and a Hard Place” had fans belting along, phones glowing like stars. By the time he closed with “Where It Ends,” the crowd was roaring, begging for more.

Oddly, festival photographers are to shoot from the photo pit, unless otherwise noted in advance, and the tour had days to notify the festival, but waited until the show had started to literally “shoo” us all back to the soundboard, waving his arms like we were farm animals. Ridiculous, unprofessional, disrespectful and piss poor planning on the artist’s team. Maybe he had a big old cold sore and didn’t want our photographer to capture it, idk. It’s a big deal because you bring different lenses if you’re shooting at a distance. Hopefully, they’ll get it together.

File Photo: Bailey Zimmerman performs in Lexington Kentucky at the Railbird Festival on May 31, 2025. (Photo Credit and Copyright; Larry Philpot/SoundstagePhotography.com)

From Small-Town Roots to Country Stardom

Bailey Zimmerman, born January 27, 2000, in Louisville, Illinois, grew up in a working-class family. Music wasn’t his first plan; he worked on pipelines and raced motocross as a teen. However, at 16, he picked up a guitar, inspired by his dad’s Luke Bryan CDs. Consequently, he started posting covers on TikTok in 2020, and his raw voice went viral. By 2021, he’d signed with Warner Music Nashville, launching a meteoric rise.

His debut EP, Leave Me Alone, dropped in 2022, followed by his album Religiously. The Album. in 2023. For example, singles like “Fall in Love” topped country charts, earning millions of streams. Since then, he’s toured with Morgan Wallen and played festivals like Stagecoach. Now based in Nashville, Zimmerman’s blend of heartland country and pop-rock has made him a Gen-Z country icon, drawing comparisons to early Eric Church.

Bands and Bandmates

Zimmerman performs under his own name, backed by a touring band with no other major affiliations. His current lineup includes:

Bailey Zimmerman – vocals, guitar
Jake Shirley – lead guitar
Chris Stevens – bass
Joey Cline – drums

He’s opened for stars like Luke Combs and collaborated with Jonas Brothers on a 2023 track, “Strong Enough.” Meanwhile, his ties to Wallen, a close friend, have sparked buzz, with the two sharing stages often. As for relationships, Zimmerman’s been linked to model Sydney Nicole Gifford since 2022, though they keep it private. No major romantic scandals with other artists have surfaced, keeping his focus on music.

Television, Film, and Awards

Zimmerman’s media presence is strong for a young star. He performed on Jimmy Kimmel Live! in 2022, singing “Fall in Love.” Additionally, his song “Rock and a Hard Place” featured in a 2023 episode of Yellowstone, boosting his profile. For awards, he’s racked up several. He won the 2023 Academy of Country Music (ACM) New Male Artist of the Year. Moreover, he nabbed the 2023 Country Music Association (CMA) New Artist of the Year. In 2024, he was nominated for a Grammy for Best Country Song for “Rock and a Hard Place.” While hall of fame talks are premature, his rapid rise suggests future honors.

Biggest Songs

Zimmerman’s tracks dominate radio and streaming, with a few defining his career:

“Fall in Love” – Written by Zimmerman, Austin Shawn, and Gavin Lucas, this 2022 hit topped Billboard’s Country Airplay chart.
“Rock and a Hard Place” – Penned by Zimmerman, Heath Warren, and Jacob Hackworth, this 2022 song hit number one, with 100 million streams.
“Where It Ends” – Written by Zimmerman, Grant Averill, and Joe London, this 2022 anthem is a live-show staple, nearing 80 million streams.

Controversies

Zimmerman’s rapid rise hasn’t been drama-free. In 2023, he sparked headlines after a public feud with rapper Machine Gun Kelly. Kelly claimed Zimmerman copied his pop-punk style, but Zimmerman dismissed it, saying he’s “just country.” Consequently, the spat fizzled, with fans split online. Additionally, in 2022, he faced backlash for canceling shows due to vocal strain, worrying fans about his health. He recovered quickly, reassuring supporters via social media. Moreover, his friendship with Wallen tied him to Wallen’s 2021 racial slur controversy, though Zimmerman wasn’t directly involved. He stayed quiet, avoiding further drama. Otherwise, he keeps a relatively clean image, focusing on his craft.

The Railbird Headliner

At Railbird, Zimmerman owned the Elkhorn Stage, closing Day 1 with fire. His set was a country-rock party, raw and real. For instance, “Fall in Love” kicked things off, his voice cracking with emotion. Meanwhile, his band kept the energy high, with Shirley’s guitar solos blazing through “Rock and a Hard Place.” The crowd, a sea of cowboy hats and raised phones, sang every lyric, their voices carrying across the infield.

His stage setup was bold—big lights, smoke, and a massive screen showing close-ups of his sweat-soaked face. As a result, the vibe felt larger than life, perfect for a headliner. During “Where It Ends,” Zimmerman paced the stage, pouring heartbreak into every note. Moreover, his banter was down-to-earth, sharing stories about his Illinois roots and late-night songwriting. For example, he told a tale about writing “Rock and a Hard Place” after a breakup, earning cheers from the crowd.

The set wasn’t flawless. A sound mix issue muddled “Fall in Love’s” intro, but the band powered through, and fans didn’t care. Additionally, some older Railbird attendees, expecting more bluegrass, seemed less engaged, but younger fans filled the gap, screaming along. Nevertheless, Zimmerman’s charisma held the stage, with “Rock and a Hard Place” turning the infield into a singalong. He threw in a cover of Chris Stapleton’s “Tennessee Whiskey,” a nod to Nashville, sparking roars.

Zimmerman’s performance was a masterclass in connecting with fans. For instance, he jumped into the crowd during “Where It Ends,” high-fiving fans and snapping selfies. Meanwhile, his band’s tight interplay kept the momentum, with Cline’s drums pounding like a heartbeat. Consequently, the set felt like a victory lap for a kid who went from TikTok to headliner in record time. His raw energy and honest lyrics made every song feel personal, like a letter to the crowd.

The show was a fitting end to Day 1, bridging Railbird’s rootsy vibe with modern country’s edge. His stories about small-town life and lost love hit hard, especially with younger fans. Moreover, his stage presence—part rockstar, part boy-next-door—kept the energy high. As a result, he proved why he’s a headliner, commanding the stage with ease. The crowd stayed locked in, snapping photos and videos, capturing the night’s magic.

As he left the stage, fans lingered, buzzing about his voice and hunting for merch. His set was a reminder of Railbird’s knack for blending old and new. Zimmerman brought heart, hustle, and a touch of Illinois grit, making the Elkhorn Stage his own. Consequently, his music echoed across the festival grounds, a bold close to Day 1. The Kentucky night felt alive as his final notes rang out, leaving fans ready for Day 2, but photographers pissed off.