Massachusetts has long been a cradle of creativity, producing some of the most iconic voices in music history. From the soulful streets of Boston to the windswept corners of Nantucket, the Bay State has given rise to singers who’ve shaken up genres, topped global charts, and left unforgettable marks on pop culture. Whether it’s the disco inferno of Donna Summer, the rock ‘n’ roll swagger of Steven Tyler, or the fresh pop energy of Meghan Trainor, Massachusetts artists have consistently proven that talent here runs deep and wide. But it’s not just about fame—it’s about influence, resilience, and the ability to connect with millions through music that moves, inspires, and defines generations. These artists didn’t just rise—they roared, often overcoming personal and industry challenges to become legends in their own right. This list dives into the top 10 most popular and impactful singers from the Bay State, celebrating the voices that have echoed far beyond New England. Whether you’re a lifelong fan or just discovering the sounds of Massachusetts, prepare to be blown away by the stories, styles, and star power of these remarkable artists. Let’s turn up the volume and explore the musical magic born right here in Massachusetts!
1. Donna Summer
Donna Summer, born LaDonna Adrian Gaines in Boston, became an unstoppable force in music and earned her crown as the “Queen of Disco.” Her voice was a rare combination of power, sensuality, and precision—capable of igniting dance floors around the globe. Summer’s rise to fame in the 1970s was meteoric, thanks to genre-defining hits like “Hot Stuff,” “Bad Girls,” and the timeless anthem “Last Dance,” which won her an Academy Award. But beyond the glitter and grooves, she was a deeply expressive artist, blending soul, rock, funk, and electronic sounds in a way that pushed pop music into new territory. Her theatrical background and gospel roots added emotional layers to her performances, while her bold fashion and commanding stage presence made her a cultural icon. Though she spent much of her career in Europe, Boston remained a crucial part of her story—shaping her work ethic and grounding her artistry. Even after her passing in 2012, Summer’s influence continues to resonate, inspiring generations of artists from Madonna to Beyoncé. More than a disco diva, Donna Summer was a transformative musical pioneer whose legacy proves that great music—and great voices—never go out of style.
2. Steven Tyler (Aerosmith)
Steven Tyler, the dynamic frontman of Aerosmith, helped craft one of the most electrifying legacies in American rock—and much of it is rooted in Massachusetts. Though born in New York, Tyler spent his formative years in the Bay State, where Aerosmith was officially born. With his unmistakable raspy wail, acrobatic stage antics, and signature scarves, Tyler became the ultimate rock showman. Alongside guitarist Joe Perry, he led the band through decades of rock classics like “Dream On,” “Sweet Emotion,” and “Walk This Way,” the latter of which broke musical barriers when reimagined with Run-DMC. That collaboration didn’t just revive Aerosmith’s career—it helped unite the worlds of rock and hip-hop in a game-changing moment. Through turbulent years of excess, breakups, and epic comebacks, Tyler remained the band’s heart and soul, his voice and charisma refusing to fade. Aerosmith’s gritty, blues-soaked sound earned them comparisons to the Rolling Stones, but Tyler’s flamboyant flair made them uniquely American. Decades later, he still commands stages with the same fire, proving that rock ‘n’ roll isn’t just about noise—it’s about energy, reinvention, and raw, unrelenting passion.
3. James Taylor
James Taylor’s gentle melodies and poetic lyrics have made him a soothing voice in American music for over five decades. Born in Boston and raised in North Carolina, Taylor’s music blends the soul of the South with the introspective spirit of New England. His breakthrough came in the late 1960s with songs like “Fire and Rain” and “Sweet Baby James,” which helped define the emerging singer-songwriter genre. His sound—a calm blend of folk, pop, and soft rock—felt like an invitation into his personal reflections, often touching on love, loss, and recovery. Taylor’s struggles with addiction and mental health gave his songs added depth, making his music a source of comfort for millions. He’s earned multiple Grammy Awards, was inducted into the Rock & Roll Hall of Fame, and remains a benchmark for authenticity and emotional clarity in songwriting. Whether performing solo or with a full band, his warm baritone and fingerpicked guitar style create a sense of intimacy few can match. Even after decades in the spotlight, Taylor’s music continues to connect, proving that quiet vulnerability can speak louder than the most amplified chorus.
4. JoJo (Joanna Levesque)
JoJo, born Joanna Levesque in Brattleboro, Vermont and raised in Foxborough, Massachusetts, stunned the world in 2004 when she released her breakout hit “Leave (Get Out)” at just 13 years old. Her voice—mature, soulful, and technically flawless—immediately set her apart from other teenage pop stars. Steeped in soul and R&B from a young age, JoJo’s influences ranged from Whitney Houston to Aretha Franklin, and it showed in every note she sang. While early fame came fast, her journey through the music industry was anything but easy. Legal battles with her label stifled her career during critical years, but JoJo’s determination never wavered. She re-recorded her early albums to regain control of her music, and her later works like Mad Love and Good to Know revealed an artist who had grown stronger, wiser, and more fearless. Her voice remains one of the most powerful in pop and R&B, effortlessly blending raw emotion with stunning control. JoJo’s story is one of resilience and reinvention—proof that true artistry always finds its way back to the spotlight, and that Massachusetts grit runs deep.
5. Meghan Trainor
Meghan Trainor, born on Nantucket Island, turned pop music on its head in 2014 with her infectious debut single “All About That Bass.” With its vintage doo-wop vibe and unapologetic message of body positivity, the song shot to No. 1 and marked Trainor as a bold new voice in the industry. But behind the catchy hooks and retro flair was a skilled songwriter who had already penned hits for other artists before stepping into the spotlight herself. Trainor’s blend of sass, self-confidence, and throwback charm felt refreshing in a landscape dominated by auto-tune and overproduction. Songs like “Lips Are Movin,” “Dear Future Husband,” and “Like I’m Gonna Lose You” showcased her knack for blending playful pop with genuine emotion. Raised in a musical household, Trainor’s early exposure to instruments and studio work laid the foundation for her distinctive DIY style. Her Massachusetts upbringing instilled a work ethic and authenticity that still fuels her career. Over time, her music has evolved, but her core message remains the same: embrace who you are, love unapologetically, and never stop dancing to your own beat.
6. Bobby Brown
Bobby Brown, born and raised in Boston’s Roxbury neighborhood, became one of R&B’s most dynamic and influential figures in the late ‘80s and early ‘90s. As a founding member of New Edition, Brown helped introduce a slick, youthful energy to R&B, but his solo career is where he truly left his mark. His 1988 album Don’t Be Cruel was a cultural phenomenon, merging funk, soul, and hip-hop into a fresh new sound called new jack swing. With hits like “My Prerogative,” “Every Little Step,” and “Roni,” Brown brought swagger, charisma, and high-octane energy to pop and R&B. He was a showman through and through—his dance moves electrifying, his vocals raw and passionate. Despite a tumultuous personal life and high-profile controversies, Brown’s impact on the genre is undeniable. He brought a gritty, streetwise edge to mainstream music and opened the door for future artists to blend genres with fearless authenticity. Through it all, his Boston roots remained a crucial part of his identity—bold, resilient, and unapologetically real.
7. New Edition
New Edition revolutionized the idea of what a boy band could be. Formed in Boston’s Orchard Park Projects in the early 1980s, the group fused R&B smoothness with pop appeal and undeniable charisma. Their early hits—like “Candy Girl,” “Cool It Now,” and “Mr. Telephone Man”—captured the hearts of teens everywhere, but it was their evolution that truly set them apart. As they grew, so did their music, tackling more mature themes and setting the stage for modern R&B groups to follow. Members like Bobby Brown, Ralph Tresvant, and the trio Bell Biv DeVoe went on to successful solo ventures, proving the group’s depth of talent. With tight harmonies, polished choreography, and a street-smart edge, New Edition bridged the gap between the Motown sound and contemporary pop/R&B. Their influence can be heard in countless acts, from Boyz II Men to *NSYNC. But beyond their music, they carried the pride of Boston with them—proof that greatness can rise from any neighborhood. New Edition didn’t just make hits—they created a blueprint that changed pop music forever.
8. Rhett Miller
Rhett Miller may be most famous as the frontman of the alt-country outfit Old 97’s, but his roots trace back to Boston, where he was born before moving to Texas. That New England birthright might seem at odds with his honky-tonk sensibilities, but it also adds a layer of introspection to his writing. Miller is known for his clever, heartfelt lyrics that often read like short fiction—bittersweet stories of love, longing, and life on the road. Whether performing solo or with his band, his music balances emotional weight with melodic brightness. Albums like The Instigator and The Believer showcase his ability to marry literary songwriting with catchy hooks. With Old 97’s, Miller helped usher in a new wave of alt-country, blending punk attitude with country twang and rock energy. Even if his connection to Massachusetts is more by birth than by upbringing, the thoughtful, writerly quality of his songs echoes the storytelling traditions of New England’s folk scene. Rhett Miller isn’t just a singer—he’s a troubadour for modern times, crafting songs that linger long after the last note fades.
9. Mark Wahlberg (Marky Mark)
Long before Mark Wahlberg became a Hollywood leading man, he made his name as Marky Mark—a hip-hop star from Boston with a chiseled physique and a rebellious streak. As the frontman of Marky Mark and the Funky Bunch, Wahlberg burst onto the scene in the early ’90s with “Good Vibrations,” a chart-topping hit driven by infectious energy and undeniable charisma. Known for his shirtless performances and tough-guy image, he was a teen idol with street cred. Though his music career was short-lived, it was anything but forgettable—blending pop accessibility with hip-hop swagger at a time when the genre was just breaking into the mainstream. His Dorchester roots shaped his public persona: gritty, no-nonsense, and fiercely Boston. Wahlberg eventually transitioned into a hugely successful acting and producing career, but his brief time in music remains a fascinating slice of pop culture. Marky Mark wasn’t just a gimmick—he was a symbol of early ’90s hip-hop’s explosion into MTV and suburban America. It was brash, it was bold, and it left a mark.
10. Cousin Stizz
Cousin Stizz, born and raised in Dorchester, is at the forefront of Boston’s modern hip-hop movement. With a calm, confident delivery and a gift for vivid storytelling, he introduced himself to the world with 2015’s Suffolk County—a mixtape that served as a gritty, heartfelt tribute to his city. Unlike many mainstream rappers who favor flash over substance, Stizz thrives in subtlety. His songs feel personal and reflective, often focused on real-life struggles, perseverance, and the importance of loyalty. Tracks like “Shoutout” and “Headlock” showcase his ability to glide effortlessly over beats while delivering sharp, understated narratives. He’s not just rapping for fame—he’s representing a community and painting a portrait of Boston that’s rarely seen in mainstream hip-hop. As one of the first Boston rappers in years to gain national attention, Cousin Stizz is shifting perceptions and opening doors. His sound is cool, controlled, and deeply authentic—a fresh voice proving that Boston’s music scene is as diverse and dynamic as any major city in the game.
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.
