Massachusetts has long been a cradle of musical innovation, giving rise to some of the most influential and genre-defining voices in American music history. From the glittering disco balls of the ’70s to the gritty rock clubs of Boston, the Bay State has produced iconic singers who’ve shaped the soundtrack of generations. Whether it’s the soulful wail of Donna Summer lighting up the dance floor, the raw power of Steven Tyler belting out rock anthems with Aerosmith, or the introspective warmth of James Taylor’s folk melodies, Massachusetts-born artists have consistently pushed musical boundaries. And the story doesn’t stop there—pop prodigies like JoJo and Meghan Trainor, R&B trailblazer Bobby Brown, and rap visionary Cousin Stizz prove that the state’s musical legacy continues to evolve with new energy and fresh voices. These artists represent a rich tapestry of sound, united by their roots in the Commonwealth and their lasting impact on global audiences. In this article, we count down the Top 10 Most Popular Famous Singers from Massachusetts—each with a unique story, a distinct voice, and a defining place in music history. Whether you’re a lifelong fan or just discovering these legends, get ready to explore the star-studded talent that calls Massachusetts home.
1. Donna Summer
Known worldwide as the “Queen of Disco,” Donna Summer was a defining voice of the 1970s dance era. Born and raised in Boston, she broke into the European music scene before returning to dominate American airwaves. With powerhouse vocals and a flair for glamour, Summer brought a new level of sophistication to disco. Hits like “Hot Stuff,” “Last Dance,” and “Bad Girls” didn’t just top charts—they reshaped dance floors and radio playlists. Her collaborations with producer Giorgio Moroder were groundbreaking, fusing electronic beats with soul-driven performance. Donna Summer’s influence extended far beyond disco, paving the way for electronic pop and dance music. Her sound, style, and unapologetic presence made her a trailblazer in both music and culture.
2. Steven Tyler (Aerosmith)
As the unmistakable frontman of Aerosmith, Steven Tyler helped turn a local Boston band into one of the biggest rock acts in the world. With his raspy voice, flamboyant style, and electrifying stage presence, Tyler became a symbol of American rock and roll. Aerosmith’s early hits like “Dream On,” “Sweet Emotion,” and “Walk This Way” made them legends, while their later resurgence in the ’80s and ’90s cemented their staying power. Tyler’s charisma and vocal range are key elements of the band’s identity. A lifelong performer, he embodies the gritty, swaggering spirit of rock music. Even today, Tyler remains a high-energy icon with deep roots in Massachusetts.
3. James Taylor
Boston-born James Taylor brought warmth, introspection, and gentle melodies to the world of folk rock. With his soothing voice and acoustic guitar in hand, Taylor captured hearts with deeply personal songs like “Fire and Rain” and “Sweet Baby James.” Though he spent much of his youth in North Carolina, his Massachusetts beginnings and ties to the region remained strong. Taylor’s music reflects vulnerability and resilience, touching on themes of love, addiction, and recovery with a poetic grace. His calm demeanor and thoughtful lyrics helped him stand out during the turbulent 1970s, and his influence still resonates with singer-songwriters across genres. James Taylor remains a master of emotional storytelling through music.
4. JoJo
JoJo emerged as a pop and R&B prodigy in the early 2000s, stunning the music world at just 13 years old with her breakout hit “Leave (Get Out).” Raised in Foxborough, Massachusetts, she combined vocal maturity with a relatable teen perspective, gaining fans instantly. Her ability to belt soulful runs with precision gave her a lasting edge over many of her contemporaries. Despite industry struggles and long hiatuses, JoJo fought to regain control over her artistry, eventually releasing critically acclaimed music as an independent artist. Her resilience, combined with undeniable talent, has earned her respect as a powerful vocalist and songwriter in the evolving landscape of pop and soul.
5. Meghan Trainor
Nantucket native Meghan Trainor burst onto the music scene with her debut single “All About That Bass,” bringing a colorful mix of retro pop, doo-wop, and body-positive messaging. With her signature throwback style and infectious energy, Trainor carved out a unique niche in pop music. Her self-produced tracks and confident lyrics showcased both musicality and authenticity, making her relatable to fans of all ages. Songs like “Lips Are Movin” and “Like I’m Gonna Lose You” demonstrated her versatility, blending modern sensibilities with vintage flair. Trainor’s Massachusetts upbringing and small-town charm remain central to her identity as she continues to inspire listeners with upbeat, empowering anthems.
6. Bobby Brown
Boston’s own Bobby Brown became a driving force in the New Jack Swing era, first gaining fame with the boy band New Edition before launching a wildly successful solo career. His 1988 album “Don’t Be Cruel” was a cultural milestone, with hits like “My Prerogative” and “Every Little Step” dominating charts. Brown’s blend of R&B smoothness and streetwise swagger made him a household name. Though his personal life often made headlines, his contributions to pop and R&B remain significant. Brown brought a new energy and edge to the genre, helping to bridge the gap between classic soul and modern hip-hop-influenced R&B.
7. New Kids on the Block
Hailing straight from Boston, New Kids on the Block redefined boy bands in the late 1980s and early 1990s. With five distinct personalities and chart-topping hits like “Step by Step,” “Hangin’ Tough,” and “You Got It (The Right Stuff),” they became global superstars. NKOTB’s choreographed routines, coordinated outfits, and catchy pop hooks set the blueprint for future boy bands like *NSYNC and Backstreet Boys. Their massive fanbase and arena-filling tours made them cultural phenomena. Even decades later, their reunion tours draw enthusiastic crowds, proving that their appeal transcends generations. For many, NKOTB remains the ultimate pop dream born in Massachusetts.
8. Cousin Stizz
As a leader in Boston’s contemporary hip-hop scene, Cousin Stizz has made waves with his laid-back flow and authentic storytelling. Born and raised in the Dorchester neighborhood, he quickly gained attention with his breakout 2015 mixtape “Suffolk County.” His music offers a raw, street-level view of Boston life, backed by minimalist beats and understated delivery. With tracks like “Shoutout” and “Headlock,” Cousin Stizz built a loyal following and earned praise from national outlets. He remains a vital voice for a new generation of Massachusetts hip-hop, proving that the state has more to offer the rap world than often acknowledged.
9. James Montgomery
Blues legend James Montgomery has been a staple of the Boston music scene for decades. With fiery harmonica skills and a gritty vocal style, Montgomery channels the raw energy of classic blues while infusing it with rock and roll flair. He formed the James Montgomery Band in the 1970s and quickly became known for his high-octane live performances and collaborations with icons like B.B. King and Bonnie Raitt. A champion of the local music scene, Montgomery has mentored countless artists while preserving the rich tradition of American blues. His passionate performances and enduring influence make him a cornerstone of Massachusetts music history.
10. Aimee Mann
Aimee Mann emerged from the Boston scene with her band ‘Til Tuesday, whose 1985 hit “Voices Carry” became an alt-pop classic. Known for her poignant lyrics and distinctive voice, Mann quickly transitioned to a critically acclaimed solo career. Her solo work, including albums like “Bachelor No. 2” and the Oscar-nominated soundtrack for “Magnolia,” showcased her talent for crafting melancholic yet sharply observed songs. Mann’s music often explores themes of emotional struggle, self-reflection, and the complexities of human relationships. With a literary songwriting style and a strong Massachusetts connection, Aimee Mann continues to be one of the most respected singer-songwriters in contemporary music.
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.
