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Top 5 Harlem Rappers of All Time!

Updated: Dec 29, 2021

By Darryl Robertson

Manhattan is one of the most affluent, densely populated hotspots in the world, known more for its financial-world prestige and its cultural cachet than its homegrown hip-hop culture. The most significant New York City-native rappers arguably originate from Brooklyn or Queens. But while there are way less MCs hailing from the neighborhood of Harlem than other NYC boroughs, Uptown has birthed its fair share of gifted wordsmiths over the years. With that, we put together a list of top five rappers from the Black mecca. (Shoutout to Harlem’s own Kurtis Blow, without whom the vast majority on this list would never have been known at all.)

1. Kool Moe Dee Kool Moe Dee, né Mohandas Dewese, made his name as a standout performer in The Get Down-era 1970s with the legendary Treacherous Three. Moe Dee’s clever, rapid-fire wordplay (see “The New Rap Language”) paved the way for his solo career after the group split in 1984.

The West Harlem MC started releasing solo singles in 1985, which led to his self-titled debut album in ’86. KMD would later drop his most well-known single, “How Ya Like Me Now,” still a catchphrase meme to this day. The album of the same name sold over a million copies and solidified his status as one of the most popular rap pioneers to achieve success during hip-hop’s first golden age, alongside upstart legends like Run-D.M.C. and LL Cool J.

Old school hip-hop heads witnessed an infamous battle between Kool Moe Dee and LL back in the late 1980s. Allegedly, the beef began after Moe Dee accused Uncle L of stealing his style and not paying enough homage to the MCs before him.

2. Big L Despite releasing only one album in his lifetime (1995’s Lifestylez ov da Poor & Dangerous), the late Big L is generally regarded as one of hip-hop’s most adept lyricists of all time. The Harlemite was killed in a drive-by shooing back in 1999 at 24 years old.

On the microphone, Big L (born Lamont Coleman) was intricate, intriguing and clever. His rap career begin in the early ’90s, when he teamed with fellow Harlem natives Cam’ron, Mase, McGruff and the late Bloodshed—collectively known as Children of the Corn. The rapper, who once emceed alongside Jay Z on The Stretch and Bobbito Show, made his first solo appearance on Showbiz & A.G.’s “Represent,” a song off their 1992 debut, Runaway Slave.

L’s most noteworthy songs include “Ebonics (Criminal Slang),” “ ’98 Freestyle” and “Deadly Combination” featuring 2Pac, all from the 2000 posthumous album, The Big Picture. Even today, Big L remains a celebrated hip-hop artist, not just in Harlem, but worldwide.

3. Cam’ron Cameron Giles, a.k.a. Cam’ron, is probably the most colorfully exciting MC from Uptown. If you’re old enough, you may remember Killa Cam as a member of Children of the Corn—alongside Mase, the late Big L, McGruff and his late cousin, Bloodshed.

At the height of the physical mixtape/CD/DVD era, Cam’ron and his Diplomats crew rose to become some of the most popular rappers in hip-hop thanks to Cam’s witty wordplay. In fact, it can be argued that for a brief period (2007-2008), Cam’ron was one of the better MCs in New York City. But not only was the former basketball player a fierce rhymer, he transcended rap to fashion and film. Cam was so popular that renowned political commentators Bill O’Reilly and Anderson Cooper tapped the Harlem kid to appear as a talking head on their programs.

4. A$AP Rocky Harlem’s Rakim Mayers—a.k.a. A$AP Rocky—is a rapper who valued style over substance on his breakthrough mixtape, Live. Love. ASAP., as well as his debut studio album, Long. Live. ASAP. But Rocky’s style isn’t typical New York.

The 28-year-old rapper has a thoughtful kaleidoscope of styles that he borrows from Southern screw music and California haze trends, which is ironic, because his parents named him after the NYC boom-bap legend, Rakim. While Rocky might not be saying anything new, he always sounds (and looks) pretty damn cool saying it. He also has feet firmly planted in the world of fashion, as a flip through any GQ magazine of the past few years will tell you.

5. Mase His weird latter-day U-turn—an international ministry, a largely ignored comeback attempt, and an even-more-ignored second comeback attempt—has obscured just how much of an impact Mason Betha made in the wake of the Notorious BIG’s passing. Harlem World (1997), a Billboard chart-topping, quadruple-platinum record, made Sean “Diddy” Combs’ second fiddle the Bad Boy Entertainment label’s golden boy, thanks to across-the-board hits like “Feel So Good.” Though nowhere near close to the lyricist Biggie was, the kid could always style on a track.


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