23 Best Massachusetts Rappers, From Boston & Other Cities

Cousin Stizz

Cousin Stizz hails from Dorchester, MA. He started freestyling as a teenager. The meteoric rise of his fellow Boston mc and friend, Michael Christmas, in 2013 motivated him to pursue rapping as a profession.

Stizz released his debut solo single, “Shoutout,” in 2014. However, it was not until his debut solo album, “Suffolk County,” a year later that he gained real commercial success.

Souleye

Souleye comes from Sturbridge, MA. He started rapping during his high school years. In 2001, Souleye began writing and touring with the Transcendental Alliance, a collective of conscious hip-hop musicians. Souleye later teamed up with underground artist, Campaign, to release the album “Soul Sessions.”

Souleye has independently unleashed ten studio albums, the most recent of which was “Hunting Teardrops” in 2021. He’s recorded and performed alongside BLVD, Bassnectar, and many more.

Big Shug

Big Shug is a rapper from Boston, Massachusetts, and the co-founder of the hip-hop duo “Gang Starr.” Unfortunately, once Shug landed in jail, Gang Starr dissolved. Guru, the other member, relocated to New York, where he recruited DJ Premier.

Upon Shug’s release, he reconnected with Guru and rejoined the Gang Starr. Shug’s first feature was on the group’s 1994 album “Hard to Earn.” He’s also collaborated with many other artists, including M-Dot, DJ Jean, and DJ Krush.

Cazwell

American rapper, songwriter, and producer Cazwell was born in Worcester, MA. He started his career in the late 90s as a member of “Morplay,” a hip-hop duo formed along with Crasta Yo. Cazwell released his debut single, “The Sex I Need,” in 2003.

To date, Cazwell has released three albums and has numerous singles. However, he’s not been short of controversy, primarily because of his sexual imagery in videos and raunchy lyrics.

Chilla Jones

Chilla Jones is a battle rapper and musician repping Boston, MA. As a teenager, Jones reigned in battle raps in Boston. Later, he shifted his attention from battle rapping to songwriting and music production.

Since then, Jones has acquired a local reputation for punchline skills and genuine and innovative song themes. To date, Chilla has released six solo mixtapes in three years. He still features in battle raps across Massachusetts, LA, New York, and Atlanta.

Gio Dee

Gio Dee is the founder of the Boston-based music group “Chef Boyz.” Dee rose to fame after social media influencer Jerry Purpdrank shared his track “Mind Yo Business” on a vine. The vine quickly went viral, receiving over a million YouTube views.

Later that year, Dee released the “Mind Yo Business EP” featuring Metro Boomin, TM88, MadeinTYO, and Lamsu. This EP’s success led Dee to curtain raise for numerous acts, including Lil Uzi Vert, G-Eazy, etc. Dee has since released two studio albums.

Esoteric

Esoteric is a veteran, Boston-based, underground rapper. He started his rap career in the early 90s after teaming up with 7L to create their debut single, “God Complex.” Soon after, the duo released “Secret Wars.” This track became more popular, thanks to Esoteric paying tribute to Marvel Comics’ heroes in well-crafted lyrics.

Esoteric and 7L then released the “Rebel Alliance” LP, which featured Force Five, Mr. Lif, and Virtuoso. In 2007, Esoteric kickstarted a solo career and released 15 albums.

Token

Token hails from Salem, MA. Sadly, Token had a troubled childhood, from being diagnosed with anxiety and depression to dealing with obesity. Nonetheless, Token was exposed to hip-hop at a young age, which inspired him to become a rapper. His outlet of writing poetry in his diary quickly transitioned to hip-hop lyrics by the time he was aged 10.

Token released his first mixtape, “The Mindstate,” in 2014. Token’s breakout video was for the “No Sucka MCs” hip-hop competition. He has since released three albums and several singles.

Dutch Rebelle

Initially from Haiti, Rebelle started rapping at around nine years old. Nonetheless, it was not until college that she decided to pursue a music career. Rebelle’s rap sound borrows heavily from R&B as she speaks about societal issues, love, and everyday struggles.

After releasing her debut album, “Married To The Music,” the Boston-based female MC had thought of relocating to Atlanta. However, she has resolved to represent her city.

Rightfully so, Rebelle can now boast she’s made it to the top, securing opening gigs for Statik Selektah and DJ Premier. In addition, she received a “Best Hip Hop Artist” award at the Boston Music Awards in 2014.

Mr. Lif

Boston rapper Mr. Lif dropped out of University to pursue music in 1994. Mr. Lif borrowed huge inspiration from iconic MCs like Rakim, Chuck D, and KRS-One. Although gangsta and party rap dominated the rap scene in the late 90s, Mr. Lif’s style concentrated on socially conscious and political lyrics.

Mr. Lif’s 1998 debut single, Elektro, drew the interest of labels Definitive Jux and Grand Royal. He worked closely with Definitive Jux to produce “Enters the Colossus” in early 2000 and a series of several popular singles. Mr. Lif also bagged Boston’s “Outstanding Rap/Hip Hop Act” for two consecutive years.

Michael Christmas

American rapper Michael Christmas a Boston Native. He started rapping during his early teenage years. At 19 years old, Michael released his first mixtape, “Is This Art?” In 2014, he constantly made waves locally and in other cities.

Michael’s popularity saw him clinch a spot on Logic’s “The Under Pressure Tour” in early 2015. Ever since, he’s released three albums titled “What A Weird Day,” “Baggy Eyes,” and “Hiding.” Unlike most Soundcloud rappers’ rowdy and trap beats, Michael’s style is more self-conscious, warm, and funky.

Top Massachusetts Rappers, Final Thoughts

Massachusetts is probably not the first state that comes to mind when you think of hip-hop. Nevertheless, that doesn’t mean the East Coast state lacks talent! This guide is a comprehensive look into the best Massachusetts rappers that have been impactful in the rap scene over the years.