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The Definitive”Top 5 MCs” Discussion

By March 29, 2009Misc, Music, Podcasts

Last week, I was asked for the millionth time to list my “Top 5 MCs of All Time”. I’ve been going through this for as long as I remember. But I decided this time to actually take a more thoughtful approach instead of spouting off the first 5 names that came to mind.

Mind you, this was probably the most difficult question that i’ve ever had to answer. Every time I came up with a name, 3 more would jump in my head. In the end, I just had to base it on some more simplified criteria:

  1. I had to think of it more in terms of my “favorites” than in terms of “best”. There is no way that anyone will ever agree on “best” because it’s solely based on opinion.
  2. I had to think of who was the best when they were at their best. Some people might think of it as a cop out, but look at this way: Usain Bolt is the fastest man in the world because he set world records at the Olympics. There might be another runner out there who averages faster times in practice, but Usain ran the fastest ever at a single point in history.
  3. I had to go with people that are recognized by the general populace. My absolute favorite rappers are probably people that you’ve never heard of.
  4. At the end of the day, I had to base it on the MCs that made impactful, permanent impressions on me for specific reasons that are described for each. I also included the name of a song which, for me, defines who they are as a lyricist. It may not always be their best or most memorable song, but it’s the one that I go to if anyone asks me to play a song by “___”.

I also include the names of some people who may have just missed my Top 5, and the reasons why. I still hold them in high regard, but I had to narrow it to my fave 5.

So feel free to discuss, argue, or whatever. This isn’t a scientific poll. These are personal opinions. I encourage you to share yours as well.

And with that, here’s the list (in no particular order):

1. Pharaohe Monch: In terms of simply being able to rap and do it on a level that nobody else can, I have to give it to Monch. Probably the best metaphorical lyricist; not to be confused with “simile MCs” – using “like” and “as” in their rhymes. The best at using full songs as metaphors and allegories for a greater concept (i.e. – “Stray Bullet”). He carries an emotional weight to his verses and has some of the best inflections in rap. Dating back to his days in Organized Konfusion, he’s also oneof the best at experimenting with different cadences – often within the same verse. Definitive song: “Agent Orange”

See also – Elzhi, Eminem, Ras Kass: Elzhi can rap his ass off. Hands down. Him and Royce 5’9”. I couldn’t put Elzhi in the top 5 because so far he’s had good verses, but I haven’t heard enough full solo songs to push him into Monch territory. In terms of putting together a solid 16, there’s a very short list of people that can give him a run for his money. Eminem, as much as I personally hate to admit, can rap circles around most. I put Pharaohe over him because a lot of songs that Eminem did were just corny. Don’t get me wrong –Eminem creates rhyme patterns that defy logic, but some of his attempts at humor just fell flat to me. Ras Kass is probably the token disappointment of this group. He should have been great. His inability to select good production is the first of his many pitfalls. I don’t really want to talk about it.

2. KRS – ONE: As much as I hate to say it for fear of stroking his ego, KRS embodies the classic definition of an MC. And I don’t say that just because of all his self-proclamations. He became one of my early favorites because he was among the first to break away from the early 80s style of Melle Mel hurrrrrRAH rapping. (I didn’t have a better way of describing it.) He was (and is) one of the absolute best at making truly “conscious” rap sound interesting. And I’m not talking about the loose definition of “conscious” either that’s been handed to Common and Kweli simply because they’re non-threatening types. KRS progressed from Criminal Minded, which was mostly a battle record, to By All Means Necessary, which was largely a topical album, which proved that good records didn’t necessarily have to be party or freestyle records. Throughout his career, he’s proven that he’s still one of the best at battling and freestyling, which are tenets of the prototypical MC, and can still make songs that force you to sit down and think. I just won’t say it to his face because he’s already a little too proud of himself. Definitive song: “My Philosophy”

See also – Chuck D, Common, Posdnuos: Uncle Chuck is / was as good as KRS in terms of making socially conscious music, but sometimes I feel like I give him as much praise as I do because he’s a part of Public Enemy. In terms of being able to rap on a purely technical level, he’s not the strongest. But I dare anyone to find someone that can bring up issues that challenge you the way he does. Common used to be good, and I know he still has it in him. Common Sense was a very good metaphorical lyricist, somewhat in the tradition of Monch. Damn good battle MC, too. Good freestyler. Then he took the path of least resistance and went for a more accessible sound. I ain’t mad at him. Get that SAG money! The only reason that I didn’t include Posdnuos in my top 5 was because I wasn’t allowed to list De La collectively. Pos and Trugoy are both lyricists that influenced a lot of my early writing, and I still hold them both in the highest regard. They’re kind of like the Wonder Twins to me – listening to both of them on the same song makes them sound better individually. It’s the chemistry between the two that makes each shine. Dave is a little more abstract while Pos is somewhat straight forward (or is it the other way around?) On an intellectual level, Pos is a rapper that I identify with: not having to exude street smarts or “swagger” for validation, and not afraid to use big words in rhymes. Anyway, De la will definitely be on my top 5 groups list.

3. Jay-Z: Let me say first off that I think of Jay as a moderately talented rapper. In terms of actual rapping ability, I probably wouldn’t even put him in my top 20. However, something has to be said about his ability to transcend normalcy and position himself as one of the greatest. Better than anyone, he has the ability to say the right thing at the right time, and infuse the most popular of popular culture into his music. Let’s be honest – his singles go hard, but most of the album cuts suck. But those singles tend to become anthems and avatars of what’s really hot in the streets. If he wanted to be a good conscious rapper, I have no doubt that he could pull it off. I wouldn’t call him the Jordan of hip hop; he was more like Bernard King who, at his best, was an unstoppable scorer. But like Bernard’s weak knees, Jay’s catalog of misses outnumbers the hits. Despite this fact, Jay has become a modern icon of hip hop and business. I have to accept that. He has an undeniable “it” factor that cannot be ignored. Of all the people on this list, I want to be most like him when I grow up. Definitive song: “You Don’t Know (Remix with MOP)”

See also – Nas, Rakim, Ice Cube: I’ll save my Nas comments for last, because they’ll probably draw the most fire. Rakim barely missed my top 5 because he can’t write hooks to save his life. His talent and influence on hip hop is undeniable. His early works should be placed in museums and studied by future generations. But he was a good writer of verses, not complete songs (for the most part). He should have taken a cue from Big Daddy Kane and stopped creating new music ten years ago. He could tour just on the strength of the classics. Ice Cube is another dude that transcends his craft. Anytime you have a college student that comes off as one of the hardest gangsta rappers ever, then becomes a socially conscious rapper, and eventually stars in G-rated movies, you have to respect that. Cube has always had some of the most emotionally charged verses that I’ve ever heard, and Death Certificate might be in my top 5 for hip hop albums. (We’ll get to that in a couple of weeks). And finally – I have a short list of most overrated rappers that goes like this: 1) Pac, 2) Biggie, 3) Nas. Admittedly, Nas would probably make my top 10 favorites list, but just barely. He benefited from a critically-acclaimed first album, which may have arguably been his best (or even last good album). It Was Written may have had more good songs than Illmatic – only because it was a longer album, but it was still not a good album. Nas has the same affliction as Ras Kass – his tendency to pick horrible production should be criminal. I do not forgive him for this. His discography is an embarrassment to his potential as a legendary artist. That whole debate about who won the Jay-Z / Nas battle is irrelevant because Nas is not 1/10th of what he should have been. “One hot album every 5 year average” is being generous. Despite the venomous nature of the preceding sentences, I do think that Nas is one of the greatest writers of our time; I’m just disappointed in the results of his work.

4. Andre 3000: If Andre Benjamin decided that he wanted to rap, he would be the best out there right now. There would not be a top 5 list for me – just a top 1. I’d put it on a t-shirt. His guest verses are better than people’s albums. He can talk about you on a song and make your song a stand out (see “Walk It Out” remix). I wasn’t supposed to like The Love Below, but it’s one of my favorite albums ever. A dude that talks as country as he does is not supposed to rap better than damn near everybody. I’m just saying. What pisses me off about 3000 is that he seems unchallenged with music. If he made an album the way that he wants to make it, I’m afraid that it would go so far over everyone’s heads that they’d miss the point. He’s kind of like Marvin Gaye without the drugs and white girls. And the exile to Europe. And dancing naked in the studio. And the cross-dressing father. But I digress. He’s a Gemini like I am, and we have the tendency to stay inside of our heads for too long. He should probably record an album today and release it in 10 years when the rest of the world has caught up to where he is. Better yet, just don’t release an album and let us always wonder “what if”. (Note sarcasm). Much like Common, I’m not mad at him for getting that “Four Brothers” and “Old School” paper. Definitive song: “Elevators” (his second verse basically sealed the deal.)

See also – Mos Def: I feel bamboozled. “Black Star” was a classic project. “Black On Both Sides” made me look at him as one of the most promising artists that I’d ever come across. And then… nothing. I don’t even remember the names of any albums after that because it doesn’t matter. Okay, so he’s an actor too. But damn – can we get any effort into making another good album? Common halfway tries. 3000 just isn’t making any albums. B.O.B.S. is one of only a handful of hip hop albums that I can still listen to all the way through without hitting the -> button. I even like “New World Water”. Shoot me. When he wants to say something, he can say it better than almost anybody. When I first heard about a “Stakes Is High” remix I wanted to protest the remaking of a classic song. I forgave them when I heard his verse. People might disagree, but I liked it. I’ll just do myself a favor and keep pretending that it’s 1999.

5. Lauryn Hill: I will take the following statement to the grave: If Lauryn Hill would have stayed on track, she would have been the greatest musical artist of our generation. Any genre. Anybody. Hands down. Why? 1) Lyrically, she had what Pharaohe, KRS, and Jay-Z have all rolled in one. The ability to mend words and syllables like Monch. The posture and presence of KRS, along with the ability to make serious topics interesting in music form. The star quality and transcendence of Jay-Z. 2) She could sing as well as she could rap. 3)The stars were aligned after the best-selling Fugees album and her debut solo. People would have followed her to the grave. She wasn’t the standout of The Fugees simply because she was better than Wyclef and Pras – that’s like saying that Jordan was better than Scott Williams or Stacey King. She was simply that good. Some might argue that she doesn’t belong here because of her abbreviated discography or because of the Unplugged album. I put her here because, in my opinion, when she was taking music seriously, nobody – man or woman – could touch her. Definitive song: “Lost Ones”

See also – Cee-Lo: To me, Cee-Lo was an Andre 3000 that could hold a note.Yes, he’s gone on to greater success with Gnarls Barkley than he ever did with Goodie Mob, but I miss the rapping Cee-Lo. He may have gotten deeper with his lyrics than 3000 and had a more outstanding voice. I originally saw him as the breakout star of the Dungeon Family, until he literally broke out. I’m not mad at him, though.

There you have it. My top 5. Feel free to discuss / argue / threaten lives / end friendships.



Founding member of K-OTIX / The Legendary KO. Unheralded jack of all trades. Spends most of his time these days creating moving pictures and writing some of the best material he's ever written. Likes dogs. Cats - meh.


  • d25 says:

    Scarface? Black Thought? early Talib Kweli and Ghosface?

  • cWJ says:

    “And finally – I have a short list of most overrated rappers that goes like this: 1) Pac, 2) Biggie, 3) Nas. ”

    Well….somebody (besides me) fine’ly said it.

  • Lat says:

    A wonderfully justified list. I can’t say I’d fully agree with it, but that’s the beauty of subjectivity right there.

    Just out of interest, why are you not a big fan of 2Pac?

    Lyrically, he was inferior to many…but the emotion he poured into his music is undeniable. The intensity of his delivery and the vivid stories he told make him particularly endearing to me.

  • afan says:

    im against comparring rappers but because all a different types of artists

    but my top 10 is.

    1. Notorious B.I.G
    2. Rakim
    3. KRS-One
    4. AZ
    5. Jay-Z
    6. Nas
    7. Scarface
    8. LL Cool J
    9. Tupac Shakur
    10. Ice Cube

    mentions to The Gza , andre 3000, big l, jeru da damaja, guru, pharoah monch, lauryn hill, queen latifah, big punisher, ice cube etc

    im sorry but theres never been anyone better then biggie or rakim or krs-one.

    if you ask krs-one, pete rock, nas, pharoah monch, talib kweli, busta rhymes, fat joe, raekwon, ghostface, method man, ice cube, snoop dogg etc they all have said biggie is the greatest rapper of all time and the most talented.

    and if you have lauryn hill in there (which i respect) then why not biggie? if its on potential then how you go past big.


    i could name 30 rappers eminem wouldnt run rings around.

    just to name a few

    jeru da damaja
    andre 3000
    pharoah monch
    big punisher
    big l
    kool g rap
    rass kass

    you want me to keep going??????

    eminems cool but he aint in the top 30 rappers of all time yet.

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