I’m not really good at the whole dramatic buildup thing, so I’ll try to keep this preamble relatively short.

First of all, this list is about great emcees, and as I’d imagine you know, great emcees are perfectly capable of making crappy records (the same way Beyonce’s albums kinda suck even though she can sing her ass off). Average emcees are capable of making great records (see: West, Kanye), so let’s not confuse the two.

What makes a great emcee? Lots of things-we can start with a great vocabulary. Add in storytelling skills, an eye for detail, a fair amount of intelligence and wit-basically the same things that make a great songwriter…EXCEPT for two qualities-charisma and “flow” or agility. These forty men and women are-I feel-the best of the best. They may not have all been commercially successful, but that’s irrelevant to me. What is relevant is the fact that I love hearing these people rap-that’s it.

Some names on this list might surprise you, some might not. You’ll note, for example, the presence of very few female emcees. Of course, it’s no excuse to say that you won’t find very many women on anyone’s list of top rappers, but still…it was hard to justify the existence on this list of many members of the opposite sex. Um, to put it more plainly, there’s only one female rapper in the entire Top 40 (for what it’s worth, I had Da Brat and  Bahamadia in the next ten).  Some of the best femcees (Jean Grae) are charisma deficient, and virtually every other girl rapper has been assisted by either ghostwriters or blatant help (B.I.G. wrote for Lil Kim, Apache and Treach wrote for Latifah.) You’ll also not find very many “new” rappers on this list. Truthfully, I can think of one rapper who debuted post-2000 that I added to this list. I just feel like lyrical dominance has fallen by the wayside in 21st century hip-hop. Even the man who many (foolishly) consider the best rapper alive, Lil Wayne, isn’t a fantastic emcee. He’s proficient, yes, and he has some killer punchlines, but if you put him head to head in a skill competition with any rapper on this list, he’s gonna lose.

So, you can go ahead and note my New York bias (the overwhelming majority of emcees on this list come from the Big Apple), you can talk about my allegiance to the “old school”, but, fuck it. I’m a guy in my mid-thirties who grew up in New York City. What the hell do you expect? As far as qualifications go: no, I wasn’t breaking in city parks or sneaking out to Union Square or Latin Quarter in the mid-Eighties (I’m too young), but I am old enough to remember hip-hop not being a commercial entity. Old enough to remember sitting in my room with my fingers alternating between the pause button and the record/play button on my boombox to catch the hip-hop being played on the radio late Friday and Saturday nights by Red Alert, Mr. Magic and Chuck Chillout. Old enough to have had my mind blown when I first heard “I Ain’t No Joke” on the radio (in Detroit!), old enough to have saved my allowance and summer job money to pick up $4 bootleg cassettes of Brand Nubian’s All for One and Ice Cube’s Death Certificate on Flatbush Avenue in Brooklyn and issues of The Source when it really was hip-hop’s Bible.

Qualifications settled? Good. Let’s rock.

40. Big L

Representing: Harlem

Of course, it’s a sad commentary on hip-hop culture that four of the 40 individuals on this list died before their 30th birthdays. Had Big L lived to make more records (he only completed one in his lifetime), it’s easy to see him having moved up 10 or 20 spots on this list. With his witty, wordy flow, he was the best emcee of two different crews: the supremely talented (well, except for Fat Joe) Diggin’ in the Crates crew and a less skilled but more commercially successful collective of Harlem emcees that included future platinum-level superstars Ma$e and Cam’ron.

39. Twista

Representing: Chicago

Style rules way over substance with this choice. There was a point in the early-mid Nineties when everyone wanted to be a speed-rapper. However, while it wasn’t so difficult to throw some nonsense phrases together and rattle them off machine-gun style (like the Fu-Schnickens), it’s much harder to retain the breath control needed to rap at 100 MPH and actually say some shit that makes sense (whether the listening public can actually figure out what you’re talking about is another story entirely). It seemed as though commercial success was gonna elude Twista forever, but with a little assistance from Kanye West, he got a brief moment in the sun. The hits have since stopped, but the skills are still there.

38. Podsnous

Representing: Massapequa, Long Island

No one in the Native Tongues was really a rhyme animal, proving my theory that you don’t have to be an excellent MC to make excellent records. Hell, Q-Tip barely scratched my Top 50. If you were to crown a rhyme champion out of the original Tongues crew, Pos would definitely take it. He, like fellow NT member Phife Dawg, actually improved with each successive album. Always an inventive lyricist, his flow eventually caught up with his words, and with songs like “Trying People” and “I Am I Be”, also proved himself as one of the most emotionally powerful emcees working today.

37. Guru

Representing: Boston

Keith Elam, the master of the monotone. The GangStarr emcee might have only had one speed, but he completely mastered that speed. His conversational flow was definitely Rakim-derived, but Gifted Unlimited Rhymes Universal put his own Beantown spin on it. He also managed to hold his own in collaboration with one of hip-hop’s all time greatest producers. Gone but not forgotten, Guru deserves props for not only his ill flow, but his unique rasp and his groundbreaking collaborations with jazz musicians in the four-part “Jazzmatazz” series.

As a sidebar: it’s crazy to think about why there aren’t more well-known emcees from Boston. After Guru and Ed O.G., who’s next on the list of popular Boston emcees? Biv, DeVoe and the Wahlbergs?

36. Pharoahe Monch

Representing: Queens

Here’s a dude that has been consistently dope for two decades. Ridiculously consistent. He was one to watch back in the Organized Konfusion days, and he’s still making dope music to this day. Not terribly crazy about his fairly recent alignment with Diddy, but at least Puff has the good sense to hire good emcees to write for him, right?

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