Before I get besieged with the “why aren’t Slick Rick, Rakim, Kool G Rap, Nas, Ghostface, Pharoahe, etc. on your list” e-mails, remember this is a list of the most UNDERRATED rappers, not the best. As the title of the post states, this is highly subjective and very little scientific research has been done. In fact, no scientific research has been done. It’s only intent is to spark discussion about some slept-on rappers and hopefully entertain for a moment as we continue to slug through the post-Labor Day malaise.

10. Chali 2na of J5

Remove Chali 2na from J5 and they’d have just been four slightly above-average MC’ rappers who really really liked The Cold Crush Brothers and really really hated “sucka MCs” . With 2na, J5 was arguably the best underground act to bubble up at out of the West Coast in the late 90s. Chalk it up to his commanding baritone and quicksilver delivery that made you instantly snap to attention. With a resounding preacher’s cadence, 2na played with syllables like a yo-yo, draping a nimble and graceful flow across a beat before snapping off an anvil-hard coda at the end of every 16 bars. Forget the Dave Matthews-collaborations of the end of J5’s run. Think back to the first time you ever heard “Concrete Schoolyard,” and don’t even try to pretend that you weren’t impressed.

MP3: Jurassic 5-“Concrete Schoolyard”

9. Treach of Naughty By Nature

Dig that old tape of Naughty by Nature’s eponymous debut out of the closet. Listen to the first five tracks and remember exactly how good Treach was in his prime. Straight from the Bricks, oozing with vicious swagger and rage, Treach rhymes circles around Kay Gee’s homicidal piano keys and sinister drums like DMX minus the the pit-bull rapper gimmick and the creepy homoeroticism. Few rappers could flip slice-of-ghetto-life tales as tragically resonant as “Everything’s Gonna’ Be Alright” and then in the next breathe drop one the 10 best party songs of all-time. Don’t believe me? Pay attention to the next time you’re at a party and “O.P.P.” comes on.

MP3: Naughty By Nature-“O.P.P.”

8. Sticky Fingaz of Onyx

There are few things lamer than the thought of a roomful of 11-year old Jewish kids slam-dancing at a junior high school dance. But it was not our fault. Onyx were that good. “Slam” was punk rock for hip-hop heads, hardcore years before M.O.P. But what sets Sticky Fingaz apart from the pack was his criminally slept-on, 2001, solo debut, Blacktrash: The Autobiography of Kirk Jones. An ambitious and frequently brilliant concept record about a felon recently released from prison and struggling to cope with terms with life on the outside, Sticky Fingaz dropped an unlikely classic.

MP3: Sticky Fingaz-“What Chu Want”

7. Royce Da’ 5’9″

If only there was some alternate 1985 where I’d never heard the names 50 Cent, D-12, Prob Stat (or whatever his name is) and the rest of the no-talents at Shady records. I stead, Eminem focused his attention on Royce Da’ 5’9, the only dude he ever rolled with that was any good. From “Bad Meets Evil” to “Boom,” to his ghost-writing a large chunk of Chronic 2001, Royce has had his share of great moments. This year’s slept-on and remarkably consistent, The Bar Exam, is probably the years best mixtape. Despite all the label drama and incarceration, Royce is still just 30 (no latte rap) and if he ever does make that album with Premier, he still has a good shot at dropping the classic he’s capable of.

MP3: Royce Da’ 5’9-“Who Want It”

6. Dres of Black Sheep

While his other contemporaries in the Native Tongues went on to become legends, Dres of Black Sheep became something of an after-thought. Sure, A Wolf In Sheep’s Clothing occasionally pops up on lists of the greatest albums of all-time, but little attention is paid to exactly how good Dres actually was. From the pinpoint gangsta-rap satire of “U Mean I’m Not” to the life lessons imparted in “Strobelite Honey” to the to train car rumble of “The Choice is Yours Revisited,’ Dres was not only one of the funniest rappers of all-time, he was also one of the few capable of straddling the line between the underground and the mainstream. I like Rhymefest well enough, but let’s be real, Dres was everything he wishes he could be.

MP3: Black Sheep-“The Choice is Yours Revisited”

5. Bizzy Bone

Name any other rapper outside of Bizzy Bone (and the rest of Bone Thugs), who could’ve turned a song about welfare check into an anthem. If Bizzy had been born 20 years earlier, he’d probably have been a weird but brilliant soul singer. Instead, he took his light-speed alto chirp and emerged as the star of the one of the 90’s most popular and yet somehow critically unsung groups. His solo career might never have gotten off the ground, but “Money,” the Twista-featured lead single off A Song For You, his solo jaunt set to drop in October is better than anything off that last tepid Bone Thugs record and proves once again that nobody beats the Biz.

MP3:Bone Thugs-“First of Tha Month”

4. Sonny Cheeba of Camp Lo


The hip-hop equivalent of Knicks legend, Walt “Clyde” Frazier, few rappers have ever sounded as slick and stylish as Sonny Cheeba. All tilted brims, fur coats, sly winks and swagger, Cheeba doesn’t attack beats, he saunters confidently across them, toying with Ski’s slinky 70s instrumentals like cats with yarn, kicking slanged-out fables about satin nights and diamond heists. Always too weird and anachronistic to fit into the mainstream, Cheeba was destined to be underrated from day one. But if you spend the time to unravel his cryptic code, Cheeba’s stories are as blindingly bright as the diamonds he raps about.

MP3: Camp Lo-“My Posse from the Bronx”

3. Edan

When I caught Edan last year at Spaceland, it was one of the most transcendent hip-hop performances I’ve ever seen. Usually when you go to a hip-hop show, it’s considered a miracle if the rappers play the best songs from the album and manage to leave their weed carriers at home. But Edan puts on a Show. Controlling the crowd, scratching turntables, freestyling and even playing the guitar and the kazoo, Edan’s live set bursts with a sense of unbridled creativity rarely seen in hip-hop. Though he’s only released two records total, 2005’s Beauty and the Beat, with its wildly original merging of psychedelia with golden-age boom-bap, established Edan as perhaps the most talented rapper to emerge from the underground in the last half-decade.

MP3: Edan-“Beauty”

2. Big Boi

It’s a little strange to include 1/2 of the most popular rap group of all-time on a list of the most underrated rappers of all-time But despite selling nearly 20 million records over the course of his career, everybody from the mainstream media to the your local neighborhood blog to your 87-year old grandmother, Esther, ignores Big Boi in favor of his more colorful, better dressed half.

No disrespect to Andre 3000, who’d probably make anyone’s Top 20 All-Time Rappers List, but the skill difference between the two is negligible. Disagree? Listen to The Love Below and then compare it to Big Boi’s far superior, Speakerboxx. Big Boi might not be flamboyant. He might not be flashy. But he remains a great rapper, one who might not be as readily marketable as Andre, but is no less responsible for Outkast’s success.

MP3: Big Boi-“War”

1. Masta Ace

It wasn’t until I fully absorbed all of Ace’s records from Take a Look Around, his Marley Marl/Mista Cee-produced debut to his 2004’s brilliant, A Long Hot Summer, that I arrived at the conclusion that Ace might be the most underrated rapper of all-time.

Ace sort of reminds me of Rafael Palmeiro (minus the steroids and the Viagra.) He’s neither flashy nor outspoken, just a hard-working veteran who you don’t really notice until one day when you check their career stats and realize that he’s one of only four players to ever knock 500 home runs and 3,000 hits.

Every one of Ace’s five records are fully realized concepts, narrated with a cinematic eye to detail and a relatable everyman persona . In a rap world dominated by larger-than-life personalities, Ace was understandably overshadowed by other Juice Crew legends like Big Daddy Kane and Kool G Rap. But while Kane and G Rap’s skills and legacies are un-impeachable, I’d argue that in his 20 years on the mic, Ace has left behind a catalogue as impressive as any of his peers.

Masta Ace-“Born to Roll”

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