The 10 Most Underrated Rappers of All-Time (As Picked in the Most Arbitrary And Subjective Manner Possible)

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.
Download:
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.
Download:
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.
Download:
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.
Download:
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.
Download:
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.
Download:
MP3:Bone Thugs-”First of Tha Month”
4. Sonny Cheeba of Camp Lo
. 
The hip-hop equivalent of Knicks legend, Walt “
Download:
MP3: Camp Lo-”My Posse from the Bronx”
3. Edan

I’m just gonna’ come out and say it: if Edan was black, he would be widely considered him one of the best rappers working today. But Edan is not black. He is white. And not Eminem-white. We’re talking Jewish kid who went to the Berklee School of Music white. We’re talking like me and Edan have the same hair style white. Which is fine for bloggers but frowned upon for rappers. Consequently, you get asinine reviews like this one.
But don’t believe what you read. 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.
Download:
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.
Download:
MP3: Big Boi-”War”
1. Masta Ace

I never thought much about Ace until earlier this year when Joey and I were compiling our Top 25 Best Hip-Hop albums list. In particular, I took note when one of my favorite bloggers, Travis of Wake Your Daughter Up named Slaughtahouse his all-time favorite and included Long Hot Summer and Disposable Arts in his top 30. Since Travis has forgotten more about hip-hop than I could ever know, I figured I needed to dig deeper into Ace’s discography.
I’d always liked Ace well enough, but hadn’t really gone much past his verse on “The Symphony” and his singles (”Born to Roll” in particular was the soundtrack to my 6th grade year, despite the fact that not only did I not even have a car, I didn’t even have a bike). But 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.
Download:
Masta Ace-“Born to Roll”
September 6th, 2007 at 5:24 am
This list is nice, JW. “Black Trash” was a pretty cool concept, espesh the “What a Wonderful World” redux.
You should be Edan for Halloween.
WW
September 6th, 2007 at 6:57 am
Ace is the man and is criminally overlooked when it comes to “complete” artists. He’s not the most lyrical, doesn’t have the best flow, but he is one of the most consistent artists out there. On “Slaughtahouse”, he was pretty complex, then dumbed it down a bit on “Sittin’ On Chrome”. He didn’t necessarily re-invent himself, but he kept up with the times with “Disposable Arts” and “A Long Hot Summer”.
And by putting Ace in the number one slot, I’ll let the Bizzy Bone pick slide…hahaha
The rest of the list looks reasonable. I can’t think that immediately comes to me that should be on the list…but then again, it’s early in the morning
September 6th, 2007 at 6:59 am
dres, d-r-e-s yes i guess i can start, if it’s ayight withchoo i’ll rip this here joint apart, back middle to the front don’t front.
and i’m going back and digging out that first naughty by nature album out now too. yoke the joka
September 6th, 2007 at 7:42 am
I’m glad you got the U-Haul’s out and upped the ante on these bitches–great lookin’ site, brother.
On a technical level, I think Treach and Royce would be #1 and #2 all time underrated. I guess I take Bizzy Bone for granted in that I never heard anyone really like him before or after but never acknowledged how dope he was (I’m still sore about Bone’s “Art of War” stealing some televised from Wu-Tang’s “Forever” in ‘97).
If Talib Kweli was half as cool and funny as Dres of Black Sheep, I might’ve bought his last 2 records.
Here’s some of my favorite underrated cats:
Milano
Roc Marciano
Breeze Brewin
Cool Calm Pete
Lil’ Fame of MOP (as an MC and Producer, he’s one of the best double threats in the game no one acknowledges)
September 6th, 2007 at 11:34 am
It’s posts like these that make me realize I had no business even touching rap and hip hop in my last post for you. I was out of my league…
Anyway, love the new digs man…the site looks great!
September 6th, 2007 at 12:25 pm
when you called royce “the only dude [eminem’s] ever rolled with that was any good,” i wanted to burst into a round of applause, but it may have freaked out the people sitting around me. he’s not underrated in my book; i think he’s arguably the best rapper alive. the bar exam is one of the two or three hip-hop releases from this year that i still listen to from start to finish, and it is, without question, mixtape of the year.
although i agree with your choices [am i the only one here who knows that charlie 2na used to be lord have mercy from the flipmode squad?], there’s one rapper that i feel is so underrated that he doesn’t even make most underrated rappers lists: cormega. dude is so ill, and his first two solo albums [the realness and the true meaning] are remarkably consistent and filled with top-notch lyricism. cormega is really the poet nas should have become before he started playing the “fake gangsta” role.
September 6th, 2007 at 12:57 pm
OTM on Chali 2na. “Concrete Schoolyard” is the song that got me into rap, and his voice has so much character…he reminds me of rap equivalent of the bass-voiced guy those 50s groups would have on songs like “Yakety Yak”
September 6th, 2007 at 1:51 pm
oh, and zilla’s OTM about lil’ fame. that dude is a monster that hardly ever gets his due.
September 6th, 2007 at 7:44 pm
i like Big Boi, but i dunno that people overlooking him in favor of ‘Dre is all that unjustified. on Stankonia in particular, ‘Dre outshines him consistently.
and before anyone says anything, yes i am aware of the rest of ‘Kast’s discography. Stankonia’s unfairly shat on though.
September 7th, 2007 at 11:20 am
love the disclaimer.
post got me thinking, in that i usually associate “underrated” with underknown, but after reviewing the list i got to reconsider my sh*t b/c you got some marquee names…
and master ace is still killin it afer all these years (nostalgia)
my contribution:
a.g.
ed o.g.
trick daddy
tash from the liks
pep love
and i concur with the brewin and cool calm pete nods. when the east is in teh house OMG
September 7th, 2007 at 3:52 pm
I love Edan, but your reference to Pitchfork’s “asinine” review is a bit disingenuous. The reviewer didn’t like that one track, but the album as a whole was one of Pitchfork’s most highly rated albums that year.
I can’t beleive I just defended Pitchfork. I’m going to go shower.
September 7th, 2007 at 11:19 pm
I’m just skimming, but I don’t think anyone has co-signed on Sonny Cheeba, yet. Allow me to second that. Part of the key to deciphering his rhymes involves knowing a thing or two about blaxploitation films, which arguably, many people do not.
Travis has me hooked on Ace’s material as well. I don’t think he plans to stop until MA takes his rightful spot in the holy trinity of rap. Guess this means Biggie, Jay-Z, or Nas will have to be displaced.
So have you done most overrated rappers yet? I love hip hop “like a fat kid loves cake”, but I can think of a lot more of those. Yeah, I’m takin’ shots at you, 50.
And a final random thought—what act of servitude does one have to undertake to become a miscellaneous apostle? Ha ha—just curious.
Hope all is well, cousin Jeff.
September 8th, 2007 at 9:08 am
Nice post. This middle-aged Jewish guy knows from where you come. Has any one in Hop Hop come as close to combining pop sensibility and street credibility as NBN? In my humble opinion, no.
You tha man. Or, as my people say, Da Mench.
September 10th, 2007 at 10:46 am
Fine work brah. Ive long thought Treach was one of the illest MCs out there to not get his proper dap. He completely wrecked their debut CD. “Uptown Anthem” etc were classic. Also agree on Edan; I was shocked I was the only cat who included him on your Top 25 Albums list. One.
September 11th, 2007 at 9:44 pm
[…] cameo rapper. The former Jurassic 5 baritone – named one of the top 10 underrated rappers by Passion of the Weiss – shows up here with Aceyalone, who is set to release his new full-length Lightning Strikes […]
September 13th, 2007 at 5:08 pm
Nice nice list; Masta Ace’s albums are always great all the way through.
It’s a shame Sticky had to follow “Kirk Jones…” up with “Decade”…because that was an AWFUL album. He was the man in Over There though, before FX cancelled it.
October 17th, 2007 at 6:04 am
Eminem…
I Googled for something completely different, but found your page…and have to say thanks. nice read….
September 11th, 2008 at 10:52 pm
definitely feeling this post…Edan is ferocious
November 8th, 2008 at 4:55 pm
Good list I always liked Sticky Fingaz and blacktrash was the greatest concept album of all time if you ask me,and I would say that Dre has always been miles ahead of big Boi on most of the albums (especially stankova) Dre badly outshines him.I agree about Edan very skilled rapper.And yes Royce is the only good rapper Eminem ever rolled with maybe Proof who had a decent flow or Obie Trice whos debut album was good.Royce is a top 30 mc if you ask me he is a great lyricist and I would say Death is Certain is a classic and I hear he is gonna be on the relapse so thats good news.Ace is a great rapper and was always the 3rd best member of the Juice Crew plus he is consistant and his catalog is almost unbeatable.Just compare his career to 2pacs.I’ll give 2pac “me against the world” and thats it his career was very inconsistant and overrated.So comparing the most overrated to the most underrated witch is ace and pac I would take underrated ace any day.Also snoop is overrated very mediocre emcee his voice and flow are the only reason he ever sold and I would take Kurupt or Xzibit over him any day.
Mine would be
underrated
10.del the funky homosaphian
9.Treach
8.Elzhi
7.Wise intelligent
6.Sean Price
5.MF Doom
4.Sticky Fingaz
3.Royce da 5′9
2.Masta Ace
1.AZ
10 most overrated
10.Chammillionair
9.Kanye West
8.Method Man-He is a good rapper when surronded by great rappers but on his own his only classic song is “bring the pain” and “method man” from 36 chambers.Tical was a huge disapointment even though it was decent it was very disapointing and not a classic.
7.Eazy-E
6.Ludacris-I’ve heard people refer to luda as underrated.I dont think so luda isnt even good.His lyrics are about as stupid as it gets and his flow is mediocre.I’ll give him Chicken and Beer as his only good album and thats it.Whats the diffrence between him and notoriously wack rapper Nelly?I cant name any.
5.Lil Wayne-hes pretty bad.From the block is hot to the carter 3 he has been as consistently bad as anyone in the game.His mixtapes arent even worth a free download there so shitty and he repeats himself way to much on his freestyles.
4.Dr.Dre(as a rapper not a producer)-His rapping skills are mediocre at best.He has dropped some notoriously wack rhymes throughtout his entire career.From “never let me slip cause if I slip,than im slippin” to “I told you im just like a clock when I tick and I tock” he is pretty bad but is usually ranked very very high.And dont even get me started on 2001 the rapping on that was terrible.The only good verse on that entire thing is eminems on “forgot about Dre” and the Xzibit verses.With 2001 the instrumental is better than the regualar version.
3.LL Cool J
2.Snoop Dogg-He has 2 good albums after Doggystyle.Thats right the doggfather and the last meal are his only other good albums.
1.2pac-I like 2pac but it is clear he is the most overrated.Overrated means rated higher than you should be so 2pac falls into that category.
November 8th, 2008 at 4:58 pm
I posted my list twice because I accidently put elzhi at 8 and not pharoah monch witch is who I wanted there.