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Listen to the Best Songs of Sierra Ferrell playlist above.
After scooping up all four of the awards she was nominated for at the 67th annual Grammy Awards in February 2025, Sierra Ferrell looks set to be Americana's biggest breakout star in many years.
For a decade, Sierra Ferrell crisscrossed the country busking, an inveterate troubadour for the modern generation. Eventually, Ferrell made her way to Nashville where her distinctive voice and songwriting began to attract fans and she signed with Rounder Records to release her debut studio album Long Time Coming in 2021.
Garnering both popular and critical acclaim for her jazz-inflected multi-instrumentalism and striking, timeless voice, Sierra Ferrell has reinvented the country wheel and shone as one of the brightest young luminaries in roots music today, bringing a little beautifully eccentric magic to everything she touches.
She won the Emerging Act of the Year prize at the Americana Honors & Awards in 2022, before scooping the Artist of the Year award and the Album of the Year award in 2024 for Trail of Flowers, before taking home all four of the Grammy awards she was nominated for in 2025, including Best Americana Album for Trail of Flowers.
She has collaborated with everyone from Margo Price and Old Crow Medicine Show to Benjamin Tod and Zach Bryan.
Here are the Best Sierra Ferrell Songs, according to Holler:
Sounding at once nostalgic and modern, Ferrell pays homage to her Appalachian roots with a sepia-toned story about an old flame. While her star ascends and her musical palette has no bounds, the waltz grounds her feet firmly in the heart of the country on this standout from her 2021 album Long Time Coming.
One of Ferrell’s numerous strengths is her eclecticism. Rather than adhering to one genre, she moves from bluegrass, to roots country, to jazz without blinking. Here, a toy piano, fiddle, steel guitar and bowed saw comprise a sonic bed for Ferrell’s sighing tale of a lover who's left.
Taken from Long Time Coming, 'The Sea' reimagines an old timey sea shanty through Ferrell's eccentrically singular vision.
Read Holler's Premiere for 'The Sea' here.
Following her 2021 debut, Long Time Coming - which turned the West Virginia-born, Nashville based artist from a train-hopping, hitchhiking vagabond to a viral sensation and award winning Americana star - her follow up, Trail of Flowers, took us even deeper into her wild imagination and wondrous world building.
The first taste of the album came with 'Fox Hunt,' as she whipped up visions of lush enchanted forests, endless flowing rivers and fertile land to a frenzied fiddling hoedown with a song about the thrill of the chase, the camaraderie of adventure, and the beauty of the natural world.
The accompanying video combined children's book illustrations with her inimitable eccentrically free-spirited styling.
Picking up the award for Best Americana Performance at the 67th annual Grammy Awards in February 2025, 'The Lighthouse' was confirmed as one of roots music's modern day anthems. Originally released on Trail of Flowers, Ferrell stripped the song back to its bare elements for an alternative version following her winning Album of the Year at the Americana Awards in 2024.
A delicately plucked yearning folk ballad, the song works as both a romantic plea to a non-committal lover and as a homespun protest song for an audience looking for comfort in an increasingly turbulent world.
"I know I'm gonna be okay, yes, I'm alright without you," she sings. "For I know there's a brighter day, for I saw his light shining through the mist."
Originally taken from the soundtrack to The Hunger Games: The Ballad of Songbirds and Snakes, 'The Garden' was among the songs on the album that helped it top the Billboard Bluegrass Albums chart.
With its moony melancholic lyrics, the song was a wistfully, metaphorical love song that likened relationships to the changing of the seasons and the cyclical way nature dies and is hopefully reborn.
Sierra Ferrell included a re-recorded fuller band version on the deluxe version of Trail of Flowers, released in January 2025.
In Ferrell’s world, the truth is painful, but more importantly, liberating; as is the case on the down-tempo, minor-key waltz that closes out her 2021 debut Long Time Coming.
Here, heartbreak is tinged with forgiveness: after discovering that a lover is unfaithful, she lets the perpetrator off the hook, singing “Now you don't have to whisper, I know”.
Ferrell’s cover of the John Anderson song from 2022’s all-star tribute to the Nashville stalwart is one of the project’s highlights.
Sounding like the old soul she is, Ferrell wraps her knowing, nimble vocal around the lyric, drawing out each note as she sings ‘‘Don’t look back in sorrow / just hope you see tomorrow”.
Taken from Zach Bryan's 2023 self titled album, 'Holy Roller' is just one of the many occasions that Sierra Ferrell has lent her inimitable vocals to another artist's work. She has collaborated with Margo Price, Diplo, The Mavericks and Old Crow Medicine Show, and more recently with Ray LaMontagne, Post Malone and Benjamin Tod.
The duet between Ferrell and Zach Bryan was a powerful and moving exploration love, loss, and redemption as the voices of two of the biggest singer-songwriters currently working in roots music blended seamlessly together to create a truly unforgettable moment in Americana history.
Taken from Trail of Flowers, this old timey barroom sing-a-long found Sierra Ferrell at her most joyful and even included real life party sound effects.
“We decided to put in some audio of my New Year’s Eve crowd at the end, so you can hear them howling on there," Ferrell says. "I always love getting everyone to howl at my shows - it’s a good, free feeling”.
Discussing the creation of ‘I Could Drive You Crazy’, Sierra Ferrell explained, “I was hanging out with some friends and we had an idea for a song where you’re telling someone, ‘I’m not good at this and I’m not good at that, but one thing I can do is drive you crazy’”.
Spare, spirited and direct, Ferrell’s unadorned performance here is a perfect fit for a song about living for love rather than money.
Ferrell’s live shows are known for being incandescent; the slightly rearranged, stripped-down acoustic version of one of Long Time Coming’s standouts captures that spirit.
While still early in her career, Ferrell has already demonstrated that she’s as fine an interpreter of songs as she is a songwriter.
As is the case with her performance of this Ray LaMontagne original. It's an excellent showcase of Ferrell’s ability to embody a range of emotions, with nothing more than an acoustic guitar and her voice.
She'd go on to collaborate with Ray LaMontagne on his own 'I Was Born To Love You' in 2022.
Taken from her 2024 album Trail of Flowers, 'Dollar Bill Bar' was a wistful tale of longing, regret and youthful recklessness, featuring backing vocals from Nikki Lane and Kristen Rogers.
Putting her own twist on the honky tonk standard, 'Dollar Bill Bar' sounded like Fleetwood Mac putting in a Friday night shift at Robert's Western World.
Taken from 2021's Long Time Coming, this bluegrass gem was about a woman realizing she’s better off alone than with someone who is unfaithful, the tune demonstrates Ferrell’s unique brand of uncontrived and authentic musicianship.
An assured performance here on GemsonVHS — think Annie Oakley with a guitar instead of a gun — helped catapult her into widespread prominence.
Taken from Trail of Flowers, Sierra Ferrell's performance of 'American Dreaming' stole the show at the 2024 Americana Honors & Awards as she walked off with the awards for Album of the Year and Artist of the Year.
A resilient rallying cry for self-care, the song has taken on a life of its own since the album's release and become a timely state of the nation address and a show-stopping centerpiece in her live set.
Ferrell is both vagabond and sage on this wistful meditation on impermanence and death, which went viral once it hit YouTube and TikTok.
“That river will flow on / Even after we’re all long gone,” she sings, skillfully deploying irresistible rounds of “Ooh-ooh-ooh-ooh-ooh, ooh-ooh-ooh-ooh-ooh’s” that are both otherworldly and infectious.
For more Sierra Ferrell, see below: