Annie Bosko, the rising country singer-songwriter known for her traditional country roots, has just released a stunning new cover of Kris Kristofferson’s classic “Help Me Make It Through the Night.” Produced by the talented Trent Willmon, this release comes on the heels of her successful duet with Joe Nichols, “Better Than You,” which has been making waves on country radio. I caught up with Bosko to discuss her inspiration behind choosing this new single, how she made it her own, and what lies ahead in her ever-growing career.
Making the Song Her Own
While “Help Me Make It Through the Night” has been covered many times over the years, Bosko’s rendition stands out for its distinct sound. “A lot of people around me were saying, ‘Oh my gosh, that song is just something special for your voice,’” Bosko shared. “It’s so unique the way you sing it.” Encouraged by friends and colleagues, she took the plunge and made the song her own.
Bosko worked closely with producer Trent Willmon to craft a sound that felt fresh and unique. He talked about making it sound like it belonged in a western movie. From experimenting with different keys to capturing the perfect voice range, every detail was thoughtfully curated. The song also features the iconic harmonica playing of Mickey Raphael, adding a touch of classic country, reminiscent of Willie Nelson.
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Influence from Her Father and Grandfather
Bosko’s deep connection to country music is also a result of her upbringing, particularly the influence of her father. Raised in a family with a strong work ethic and a love for traditional country music, Bosko grew up with a clear sense of dedication. “He’s got a work ethic like no other,” Bosko said, sharing the story of her grandfather’s immigrant background and the sacrifices his family made to build a better life in America.
Her father’s appreciation for country music, particularly the faith, family, and patriotism at the heart of many songs, shaped Bosko’s own musical tastes and career choices. But it wasn’t just her dad’s influence—Patsy Cline’s voice struck a chord with Bosko at a young age, sparking her own passion for music. From there, it was only a matter of time before she knew country music was her calling.
Success and Big Milestones
Bosko’s career has been gaining serious momentum, with her duet with Joe Nichols making it to the top five most-added on country radio. “It’s almost surreal,” she said, reflecting on her lifelong dream of having her music embraced by radio and fans. For her, country radio has always been a guiding force, and hearing her own songs on air is a dream come true.
This year, Bosko is poised for even bigger moments. She’ll perform at major festivals like Stagecoach and the Houston Rodeo, two stages that she’s dreamed of playing since her early days. And in the fall, she’ll release her first full album, something she’s been working towards for years. “It’s a dream come true,” she said, adding that her fans can expect a new single every five weeks leading up to the album’s release.
What’s Next for Annie Bosko?
With her new music on the way and performances at iconic venues ahead, 2025 is shaping up to be a breakout year for Annie Bosko. From her cover of “Help Me Make It Through the Night” to her upcoming album and live performances, it’s clear that this rising star is just getting started.
