The 10 Most Legendary Rappers From New York City

Anti-hero, idiosyncratic, and The Greatest of All Time. Game recognizes game. And when your name appears 99.99 percent of the lists of greatest rappers, you just might be the greatest.

No matter how much time passes, there is little doubt that Notorious B.I.G. will remain one of the sturdy pillars of the genre and culture. At age 24, and with only two studio albums to his credit, Christopher Wallace had a definite “it” factor – that certain something that today might be called “swag” or might have earned him a privileged place among living icons. Still, in death, his iconic status lives on. And in hip hop, where there is mutual respect among MCs but always a competitive nature, most rappers can agree that Biggie left an indelible mark on them as artists and people.

Essential Listening: Ready to Die – “Respect”

The undisputed King of New York and the embodiment and personification of the American rags-to-riches dream. From the Marcy projects of Bed-Stuy to one of the most influential people, let alone musicians in the world, Jay Z’s importance is unquestionable. His music sales alone top $100 million, and his other successful, entrepreneurial endeavors have taken him to Forbes-level wealth. His polarizing relationship with pop star Beyoncé only further solidifies his firm grip on the crown. But really, what puts him atop this list are his lyrics. His uncanny ability to string together clever couplets with double meanings, move within his own words and stop-start, all while bridging outrageous rhyme schemes is otherworldly.
Essential Listening: The Blueprint – “Renegade”

The storyteller, the sage, the prophet. The cunning, tactical ease with which Nas is able to vocalize a story and report the situation, shed his “next Rakim” laud and made him prolific in his own right; he is, hands down, one of the best MCs ever. His distinctively stylish method of delivery – intelligent but effortless – clearly comes from his free-flow jazz upbringing as the son of musician Olu Dara, and a reflection of the Crown Heights neighborhood of Brooklyn. Fluid and highly literate without pretension, his debut album, Illmatic, will forever hold every MC to a higher standard.

Essential Listening: It was Written – “The Message”

It’s fairly well-known that one of the most influential American contemporary artists came from Harlem. His original moniker, MC New York, would have certainly changed the outcome of circumstances that led to his murder in 1996, in a bitter feud between rival hip-hop coasts. Tupac began his artistry in theater drama; he was accepted into the Baltimore School of Arts as a teenager after prodigal success in the theaters of Harlem. He was also raised by the radical political views of his mother, who was a key player in the 1970s Black Panther organization. Tragedies are often the most crucial stories, and his is one of extreme enduring love through absolute tragedy.

Essential Listening: All Eyez on Me – “All Eyez on Me”

Mos Def is the reigning king of backpack, underground indie-rap. He, along with co-pilot Talib Kweli, forced the music industry to coin the term “conscious” to describe a new wave of hip hop blasting through suburban skate parks and dorm rooms across the U.S. From Brooklyn became a new hope and a style that could hold its own on the block or in the classroom. Mos Def strayed from the violent, dollar sign rhymes of his contemporaries and brought with him something new, stylish, smart, and genre-defying.

Essential Listening: Black on Both Sides – “Mathematics”

Imagine a world where South Jamaica Queens’ own 50 Cent doesn’t go on to movies, TV, boxing promotion, and Vitamin Water flavoring. The reason he was noticed and endorsed by Eminem wasn’t his mainstream media potential; it was his ability to write devastating disses and his smile-through-fangs style. Ignoring his obvious commercial success, going back to underground mixtapes from the early 2000s, you can hear the desperation and like-it-or not attitude that set him apart. The more you dig into his history the more you can see that his debut album, Get Rich or Die Tryin’, is a carefully constructed mantra.

Essential Listening: Get Rich or Die Tryin’ – “Life’s on the Line”

There is a reason you can find this prolific MC atop every Greats of Hip Hop list. Be it solo or with Eric B, Rakim is the originator of NYC hip-hop. Rakim’s rhyming deviated from the simple rhyme patterns of early 1980s hip hop. His free-rhythm style ignored bar lines and forever changed the rules on rap style, and 1987’s Paid In Full is one of rap music’s first albums to receive commercial success. Rakim’s more laid-back and funky style, a soundtrack for the times, would set a trend that still echoes today.

Essential Listening: The Master – “When I Be On The Mic”

Duo Mobb Deep come from Queens. Pairing evocative beats and cinematic rhymes that disclose the dark side of New York’s urban landscape, Prodigy is the gritty voice of the Queensbridge projects. His rhymes are unflinchingly bleak, comparing the projects to the front lines of war, the self-proclaimed “mix of vodka and milk.” A groundbreaking movement away from the braggadocios lyrics topping hip-hop charts, Prodigy and partner Havoc, revel in the realness of the world around them.

Essential Listening: The Infamous – “Survival of the Fittest”

From the Park Hill Projects of Staten Island, he’s colloquially known as “Killa Hill.” Oftentimes overshadowed by his polarizing charisma, the one and only Method Man is the true lyrical talent that birthed the Shaolin star. The only rapper to be featured on Biggie Small’s debut album, Ready to Die, he clawed his way from a Statue of Liberty souvenir gift shop to numerous Hollywood endeavors. It is the roots of his emergence as a staple of the Wu-Tang Clan and his explosive collaborations with Redman that made him a stand-alone MC.
Essential Listening: Tical – “Bring The Pain”

Dubbed “The Genius,” blending scientific theory with melancholic East Coast beats, GZA comes from Brooklyn, though he is known for his part in the birth of Staten Island’s Wu-Tang Clan. He is known as the group’s “spiritual head,” being both the oldest and the first within the group to receive a record deal.

He also flexed some acting chops, hilariously appearing in The Chappelle Show and with his cousin RZA in Director Jim Jarmusch’s Coffee and Cigarettes, opposite Bill Murray. He has also taken his scientific mind to the classroom, taking part in an MIT workshop on the “evolving culture of science engagement.” In 2013, he spearheaded a New York City-wide public school program that combines science education with hip hop.

Essential Listening: Liquid Swords – “4th Chamber”
Honorable Mentions: Cam’ron, AZ, Big L, Noreaga/Capone, Jadakiss, Ghostface Killa, Guru, Big Pun, Busta Rhymes, and KRS One.