When you think of Vermont, you might picture maple syrup, scenic mountains, and cozy small towns—but this picturesque state also has a surprising musical heartbeat. Nestled in its valleys and echoing through its forests is a rich legacy of talent that has shaped the soundscape of everything from indie folk to R&B, rock, and even Broadway. Vermont may be small in size, but it’s produced some truly big voices.
From chart-topping pop sensations to Grammy-winning bluegrass stars, and from soulful singer-songwriters to genre-defying rock legends, the Green Mountain State has nurtured artists whose influence resonates far beyond its borders. Some were born here, others found inspiration in its serene landscapes—but all of them share a deep connection to Vermont’s creative spirit.
In this article, we’re counting down the Top 10 Most Popular Famous Singers from Vermont—a mix of household names and critically acclaimed artists who have helped put this quiet state on the musical map. Whether you’re a lifelong Vermonter or just discovering these voices for the first time, prepare to be inspired by the incredible talent that’s emerged from one of America’s most unexpected musical hotspots. Let’s turn up the volume and explore the sounds of Vermont! 🎶
1. Taylor Swift
Taylor Swift’s transformation from a teenage country singer-songwriter into a global pop powerhouse is one of music’s most compelling journeys. Bursting onto the scene with heartfelt ballads and acoustic guitars, she quickly earned a reputation for her sharp lyrical storytelling and emotional depth. But Taylor never stayed in one place creatively. She boldly crossed genres—moving from the twang of Fearless to the sleek synths of 1989, the dreamy introspection of folklore, and the stadium anthems of Midnights. Each era reveals a new layer of her artistry, often mirroring her own personal growth. Beyond her music, Swift’s battle to regain control of her master recordings sparked a broader conversation about artist rights and ownership, reinforcing her status as a fearless advocate in the industry. Her “Taylor’s Version” re-recordings are not only chart-topping successes, but cultural events that reaffirm her bond with fans. Whether writing tear-streaked breakup songs or empowering self-love anthems, Taylor taps into universal emotions with unmatched precision. She’s not just a hitmaker—she’s a cultural architect, shaping how pop music is written, experienced, and remembered. With every album, Swift proves she’s not just evolving—she’s leading the way.
2. Beyoncé
Beyoncé isn’t just a performer—she’s a phenomenon. From her beginnings in Destiny’s Child to her reign as a solo artist, she’s crafted a career defined by reinvention, excellence, and unshakable presence. Each chapter of her musical journey—from the sensual empowerment of B’Day to the deeply personal narrative of Lemonade—is marked by bold artistic choices and rich cultural commentary. She doesn’t simply release music; she builds immersive experiences that fuse visual storytelling, social activism, and musical innovation. Albums like Renaissance continue that legacy, honoring dance music’s roots while carving out new sonic territory. Beyoncé is also a champion for Black identity, womanhood, and empowerment, using her platform to uplift marginalized voices and spark meaningful conversations. Her performances—whether at Coachella, the Super Bowl, or surprise drops—are masterclasses in precision, passion, and purpose. With a voice that can roar or soothe and choreography that mesmerizes, Beyoncé exemplifies what it means to be an artist in every sense. Her influence spans generations, genres, and continents. She’s not just in the spotlight—she defines it. And as long as she keeps creating, she’ll continue shaping the future of music and culture.
3. Drake
Drake has become the defining voice of modern hip-hop by blurring the lines between vulnerability and bravado. Since his 2010 debut album Thank Me Later, the Toronto native has continually pushed the boundaries of rap and R&B, forging a sound that feels both intimate and larger-than-life. He pioneered a style of confessional lyricism—part stream-of-consciousness, part late-night diary entry—that connects deeply with fans. Whether delivering smooth melodies on tracks like “Hold On, We’re Going Home” or unleashing hard-hitting bars on songs like “Started From the Bottom,” Drake moves seamlessly between moods and genres. His albums—from the emotional depth of Take Care to the genre-hopping ambition of Views and Honestly, Nevermind—have kept him at the forefront of pop culture for over a decade. Beyond his music, Drake’s influence can be seen in the rise of melodic rap, his dominance on streaming platforms, and the global success of artists he’s championed. He’s a tastemaker, a trendsetter, and a master of reinvention. With an uncanny ability to stay ahead of the curve while never losing sight of his core appeal, Drake’s reign shows no signs of slowing down.
4. Billie Eilish
Billie Eilish exploded into the mainstream like a whisper cutting through the noise. With her ethereal vocals, moody soundscapes, and hauntingly honest lyrics, she carved out a space in pop that felt entirely new. Collaborating closely with her brother and producer Finneas, Billie’s music eschews glossy pop conventions for something darker, weirder, and more human. Her debut album WHEN WE ALL FALL ASLEEP, WHERE DO WE GO? stunned the industry, winning multiple Grammys and signaling a shift toward minimalism and emotional rawness in pop. But Billie isn’t just about music—her signature style, which embraces comfort, autonomy, and a rejection of objectification, has made her a Gen Z icon. Albums like Happier Than Ever show her growth both as a writer and a person, revealing layers of frustration, introspection, and newfound confidence. She’s unafraid to tackle themes like mental health, fame, and identity, giving voice to a generation wrestling with similar issues. Billie Eilish has redefined what it means to be a pop star in the 21st century: genre-less, boundary-pushing, and unapologetically herself.
5. The Weeknd
The Weeknd’s rise from anonymous mixtape curator to global music innovator is one of the most compelling narratives in modern pop. Born Abel Tesfaye, he started by releasing shadowy, R&B-laced tracks that felt like late-night confessions—dark, seductive, and emotionally complex. His early trilogy—House of Balloons, Thursday, and Echoes of Silence—cultivated a mystique that drew in devoted fans. As he stepped into the spotlight, he never abandoned that atmospheric edge. Instead, he fused it with pop accessibility, creating megahits like “Can’t Feel My Face,” “Starboy,” and the retro-synth anthem “Blinding Lights.” His albums are more than collections of songs—they’re conceptual journeys filled with cinematic flair and emotional nuance. With After Hours and Dawn FM, The Weeknd redefined how pop and R&B can intersect, delivering visuals, narratives, and sonics that feel immersive and surreal. His falsetto is unmistakable, his vision uncompromising, and his artistry continuously evolving. Whether crooning over sparse beats or crafting dancefloor-ready anthems, The Weeknd remains a shape-shifter who pushes boundaries while staying true to his enigmatic core.
6. Olivia Rodrigo
Olivia Rodrigo burst onto the global music stage with all the rawness and honesty of a handwritten journal. Her debut single “drivers license” quickly became a cultural phenomenon, capturing the heartache of young love with piercing clarity. That same emotional depth defined her debut album SOUR, a genre-spanning blend of pop, punk, and indie that resonated powerfully with a generation navigating heartbreak, identity, and self-discovery. Olivia’s greatest strength lies in her songwriting—unflinching, relatable, and emotionally articulate beyond her years. Songs like “good 4 u” and “traitor” tap into the turbulence of teenage emotion with both fury and finesse. But she’s no fleeting teen idol. With her sophomore album GUTS, Olivia proved she could evolve while staying authentic, delivering deeper lyrical insight and even more sonic variety. Her music combines the raw energy of early 2000s alt-pop with modern sensibilities, and her fearless vulnerability has made her a role model for Gen Z and beyond. Olivia Rodrigo isn’t just singing about youth—she’s shaping its soundtrack in real time.
7. Kendrick Lamar
Kendrick Lamar is not only one of the most respected figures in hip-hop—he’s one of the most important voices in contemporary music, period. Hailing from Compton, California, Kendrick blends intricate storytelling, fearless introspection, and biting social commentary in a way few artists ever have. Albums like good kid, m.A.A.d city, To Pimp a Butterfly, and DAMN. are not just critically acclaimed—they’re cultural landmarks. Through them, Kendrick dissects complex topics like systemic racism, generational trauma, personal identity, and spiritual struggle with lyrical brilliance and unmatched flow. His Pulitzer Prize-winning album DAMN. solidified his role not just as a rapper, but as a cultural critic and modern-day poet. Kendrick’s music doesn’t pander; it challenges, provokes, and enlightens. He disappears between projects, but when he returns, it’s always with something urgent and meticulously crafted. Whether delivering fiery political bars or personal confessions, Kendrick speaks with a conviction and clarity that commands attention. He’s a generational talent whose impact goes far beyond the charts.
8. Doja Cat
Doja Cat is one of the most unpredictable and inventive artists in today’s pop and hip-hop landscape. Emerging from internet fame with the viral hit “Mooo!”, she quickly proved she was far more than a novelty. With each release, Doja has demonstrated a knack for blending rap, R&B, pop, and dance music into something uniquely her own. Albums like Hot Pink and Planet Her showcase her impressive vocal range, razor-sharp rhymes, and infectious production choices. But it’s not just her music that turns heads—her visuals, performances, and social media persona all reflect a fearless creativity that keeps fans and critics guessing. Doja Cat is equally comfortable making a TikTok-ready bop as she is experimenting with darker, edgier aesthetics, as seen on Scarlet. Her ability to shape-shift, paired with a clear artistic vision, has made her one of the most dynamic artists of her generation. She’s a digital native and a true showman, fusing humor, sensuality, and innovation into a brand that defies categorization. Doja doesn’t just follow trends—she invents them.
9. Bad Bunny
Bad Bunny has flipped the script on Latin music—and the global music scene at large. Born Benito Antonio Martínez Ocasio in Puerto Rico, he’s brought reggaeton, Latin trap, and countless other genres into bold, uncharted territory. His breakthrough came not just from his catchy rhythms and genre-bending sound, but from his authenticity and refusal to conform. Albums like YHLQMDLG, El Último Tour Del Mundo, and Un Verano Sin Ti are eclectic masterpieces that effortlessly mix romance, rebellion, and cultural pride. Bad Bunny raps about love, loss, politics, and Puerto Rican identity with a voice that resonates far beyond Spanish-speaking audiences. He’s also a fashion icon, fearlessly challenging gender norms with his clothing choices and public statements. Whether he’s headlining Coachella or collaborating with global superstars, Bad Bunny remains unapologetically himself. He’s not just dominating charts—he’s redefining what Latin music can be and who gets to shape its future. With every boundary he breaks, he paves the way for the next wave of artists to do the same.
10. SZA
SZA has carved out a space in R&B that feels simultaneously dreamy, raw, and deeply introspective. With her breakout album Ctrl, she redefined what vulnerability sounds like—offering poetic meditations on love, insecurity, and personal growth through lo-fi beats and unfiltered lyrics. Her music is more than sound; it’s feeling. SZA’s voice, soft and airy yet full of emotion, carries an authenticity that’s rare in any genre. Her long-awaited follow-up, SOS, delivered even more emotional complexity and genre exploration, proving that she’s not content with staying in one lane. From trap-inspired anthems to acoustic ballads, SZA writes like someone who’s cracked open her soul for the world to see. And the world has responded in kind. Her songs don’t just top charts—they become personal soundtracks for fans navigating life’s messiness. With an unmatched ability to articulate modern womanhood’s contradictions—confidence and doubt, longing and liberation—SZA has become a defining voice of her time. She doesn’t shout her truth; she sings it softly, and it echoes loud.
Samuel Moore is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
