The following are key rappers who have been widely influential—creating and developing the techniques that the majority of later rappers use. Therefore this not a “best of all time” list (though all of these artists could arguably be on such a list), but a list of those who have made hugely significant contributions to the art form of rapping.
Through these influential figures, you can get a picture of how the craft was created—how more simplistic techniques were developed into complex forms.
“Waves” of Rappers
There are essentially three waves of rapping and rappers. The first laid the foundations during the old school in the early 1970s to 1984, the second developed and perfected the techniques in hip-hop’s golden age of 1986 to 1994, and the third wave from 1995 onwards use the techniques that have already been created.
The rappers in this article are from the first two waves, as these are the eras when the majority of the innovation took place, influencing everything that came after. While there are many very skillful rappers from the third wave, they mainly use the core techniques that were developed in the previous two waves, with only occasional additional innovations.
Wave 1: The Foundation (old-school rappers, early 1970s to 1984)
There are three main foundational rappers from the old school: Melle Mel (of Grandmaster Flash and the Furious Five), Grandmaster Caz (of the Cold Crush Brothers), and Kool Moe Dee (of Spoonie Gee and the Treacherous Three).
Doug E. Fresh
I mean for me, man, the three best MCs of all time is Melle Mel, Kool Moe Dee, and Grandmaster Caz. Hands down, as far as foundation. I know all their rhymes…. The funny thing is, each one of their styles are very different, like Moe Dee was technically extreme, I mean like sharp, and then slickness and flavor was Caz, [and] Melle Mel was spiritual.
These three are the most studied of the old-school rappers, especially by the rappers who later developed and mastered rapping’s more advanced techniques. They are often mentioned together when artists from the golden age talk about their influences.
I knew that Melle Mel and Caz and Moe always put something into their work, and every time I sat down to write a rhyme I always wanted to make sense and show that I went to school and I took language and social studies and that I knew how to write a book report. That’s the way I took my rhymes, because of those guys. Listening to them coming up was the best thing that could have happened to me.
Kool G Rap also mentions this trio of old-school rappers together, along with his personal mentor, Silver Fox.
Kool G Rap
I’m a student of the Grandmaster Cazs, the Melle Mels, the Kool Moe Dees, Silver Fox from Fantasy 3 … so when people took to me, they were really taking to a part of each of those rappers, because that’s where G Rap was branded from. These were the dudes that influenced G Rap to rap the way he raps or to even just have the motivation to want to stand out from everybody else and not only be different but be the best at what I do—it was inspired by those rappers.
Melle Mel was arguably hip-hop’s first elite rapper and became prominent around 1978, before rapping had started to appear on records.
Other old-school rappers note that Melle Mel was responsible for changing rapping from simple call-and-response chants spoken over the music to the “on-the-beat” and “in- time-with-the-music” rapping style that became the basis for everyone else— where the focus was more on the lyrics rather than just getting a crowd hyped up with basic chants or talking.
Kool Moe Dee
When you talk about Melle Mel, you’re talking about … a series of firsts. First of all, he’s the first MC to explode in a new rhyme cadence, and change the way every MC rhymed forever…. Melle Mel’s [on-the-beat] cadence is still the rhyme foundation all MCs are building on. Mel flipped the cadence from the simplistic call-and-response style, and added a rhythmic rhyme punch-line style.
Kid Creole, Grandmaster Flash and the Furious Five
[Our DJ, Grandmaster] Flash, would have guys on the microphone who’d just get on there and say his name, haphazard, no real talent being displayed. And my brother [Melle Mel] … I don’t know, somehow or another he got in his head that he was going to try to make up his own rhymes, and that’s what he did. There was no real outside force that made us write rhymes, because nobody was writing rhymes. [Earlier rappers], they said phrases; they didn’t say rhymes. They would say, “On down to the last stop.” “More than what you paid at the door.” Stuff like that. And when we started writing rhymes, we put sentences together.
When rap began being recorded and released on record labels, Melle Mel brought in political content with “The Message” in 1982 and “White Lines” in 1983 (both under the group name Grandmaster Flash and the Furious Five), at a time when rap was mostly party content and braggadocio.
Melle Mel from the Furious Five—he was one of the first MCs to take it from just a party atmosphere and talk about what’s really going on in the world. And how fucked up New York is and what they see in their hood, and you still can dance to it. To this day when “The Message” comes on you can dance to it, but still the lyrics were incredible, plus he was just an ill performer. Melle Mel, man, he’s a beast. He should be given some type of award.
Mel, he was like a street poet then, like the way he seen what was going on in the inner city, from “White Lines” to “it’s like a jungle….” Melle Mel was the conscious rapper then, from political, to what he seen going on in the neighborhood.
Melle Mel’s voice is still one of the most commanding and unique in hip-hop and he had a high level of precision with his rhythm and timing in an era when a lot of other rappers often had a looser, more casual approach to their delivery.
Chuck D, Public Enemy
I liked the guys with the great voices, guys like Melle Mel—I thought they were unbelievable.
Mel was like the lion of the game, the lion’s roar.
Melle Mel is one of the best examples of the original style of rapping and the fundamental techniques, such as staying on beat, projecting the vocals, and rhyming words while still conveying a strong message. “The Message” is his most famous track, though the majority of his old-school records are great examples of an early innovator and master.
Melle Mel was always using big words and ill rhythms, but he’d break it down and get a little political, too, like “White Lines” or the joint he did on Beat Street. He was scientifical with it.
Kool Moe Dee
Kool Moe Dee was a member of the old-school rap group Treacherous Three and is primarily known for his intricate rapping style. Of the three key figures of old-school rap, Kool Moe Dee was the one who focused the most on pushing forward the technical aspects of rapping, coming up with more sophisticated rhythms and rhyme schemes. He helped introduce fast rapping on Treacherous Three’s song “The New Rap Language.”
Special K, Treacherous Three
One day Moe had said this fast rhyme … he invented that, I got to give him credit for that.
By laying the groundwork in the old school for later rhyme technicians such as Kool G Rap and Big Daddy Kane to build on, Kool Moe Dee’s early innovations set the stage for further developments in intricate rap writing and delivery.
Big Daddy Kane
There were great lyricists before [the golden age rappers]. I don’t know if you’ve heard any of the Kool Moe Dee stuff when he was with the Treacherous Three, but Kool Moe Dee was an incredible MC, early ’80s, late ’70s. It’s like when you listen to Rakim, you can hear a heavy Kool Moe Dee influence.
Many MCs admire the level of sophistication he brought to rapping, noting that he drew from his college education to broaden rap’s vocabulary and word play.
[Kool Moe Dee] was very influential on me. Back in those times—the vocab and all that, the big words. Treacherous Three tapes, listening to them … coming out as an artist, that just inspired me a lot.
From Kool Moe Dee, you got the ferocious type of style, but at the same time he was a conscious cat. Moe Dee went to college and kinda incorporated what he was learning in college into his songs. You could tell right away by listening to his metaphors, listening to his four-five- syllable words, and the way he put things together.
DJ Easy Lee, Treacherous Three
He was one of the earliest rappers to have a college degree, so he was well spoken and very articulate.
Moe Dee was also one of the few old-school rappers who had significant success going into the golden age of hip-hop as a solo artist. This later success was helped by his proficiency as a battle rapper—he was involved in some of the most famous battles in hip-hop history, including a live battle with Busy Bee that was widely circulated as a tape recording in the early 1980s, and a battle with LL Cool J over the course of several records during the late 1980s.
I love Kool Moe Dee, I think he’s amazing because he actually made the [rap] battle become what it is, because he took battling to such a whole different level. And he’s such a lyrical beast.
As far as MCs are concerned, Kool Moe Dee was like the top dog at that time. Those infamous rap battles he used to have with Busy Bee were enormous to me when I was young.
He was a beast too, I’m sure everybody heard the Busy Bee and Moe Dee battle. Moe Dee kinda enforced that ferocious type of MCing.
A member of the Cold Crush Brothers, Grandmaster Caz completes the trio of early rappers who set the foundation. Out of the old-school rappers, his legacy is one of the hardest to get to grips with, mainly because there aren’t many official recordings by him or the Cold Crush Brothers during their most prominent period.
Many ’80s and early ’90s rappers listened to bootlegged tapes of live recordings from the Cold Crush Brothers in order to study Caz’s techniques—he was particularly influential in shaping how group routines were written (where multiple rappers rap back-and-forth together), a skill later built upon by Run- D.M.C. One of the best places to witness Caz and the Cold Crush Brothers in action is on the 1983 Wild Style film, as there is limited access to other recordings.
Kool Moe Dee
There were tapes being made … Cold Crush is legendary for their tape sales. With those tapes, 90 percent of the MCs that came from the mid ’80s, early ’90s studied the Cold Crush. They studied the old school MCs. Caz definitely, without question, being the lead man [of the Cold Crush Brothers] and the point man in the equation, was like the prototype for all of the studying that was going on.
Somebody will sneak a tape in or somebody will get a tape up in the DJ booth and you make the tape, you tape the show and bring it out in the streets, sell it six to ten dollars—a lot of tapes were sold like that. My first tape I bought was the Cold Crush tape, six dollars I paid for it, and it was like an album to me.
Some of his most famous and quoted lyrics were infamously uncredited and used by Sugarhill Gang’s Big Bank Hank on “Rapper’s Delight,” one of the very first and most influential rap recordings.
For many later rappers, “Rapper’s Delight” was one of the first records that they heard with rapping, and so Caz’s influence can also be felt through that record—whether listeners knew it was partially written by him or not. He is named by many golden age rappers as a direct major influence—Rakim, Kool G Rap, and Big Daddy Kane specifically mention listening to Caz to help develop their styles.
Big Daddy Kane
The flow that I use, I really developed my rap style in the mid-’80s based on Grandmaster Caz from the Cold Crush Brothers, from listening to him. That’s like really who I pretty much patterned my style from, and I just took it to another level once I had the opportunity to get out amongst the world myself.
I’d also make sure I always saw the Cold Crush Brothers. [Grandmaster] Caz was a big influence on me. Grandmaster Caz was like one of the wittiest cats that I heard. His stories and his rhyme style … you sat there and you would say, “yo, this kid is nice,” but at the same time you had a little smile on your face ’cause half the things he was talking about was half the things you wanted to do and half the things you wanted to be. So Grandmaster Caz, he was just a witty cat and you could tell sometimes when he’s rhyming, he’s got a smile on his face, so he just kinda made rap feel good.
Wave 2: Development and Mastery (golden age rappers, 1986–1994)
The second wave of rappers are from hip-hop’s golden age (1986–1994). These four rappers made huge strides forward in developing and perfecting rapping techniques: Rakim (of Eric B. & Rakim), Big Daddy Kane (of the Juice Crew), Kool G Rap (of the Juice Crew), and KRS-One (of Boogie Down Productions).
As with the three foundational, old-school rappers, the four of them are often grouped together when later rappers are discussing their influences.
Rock, Heltah Skeltah
Kool G Rap, Big Daddy Kane, Rakim, KRS-One … was basically what shaped my shit when I was young.
Tajai, Souls of Mischief
I grew up in the era where the best guys were like Big Daddy Kane, Kool G Rap, and Rakim—those dudes where you can’t listen to their rap once and figure out what they’re saying.
I studied KRS-One, Rakim…. Kool G Rap from the Juice Crew kind of set the standards for me as far as what was considered a dope verse and dope rhyming…. I just kind of analyzed their styles.
RZA, Wu-Tang Clan
Rakim, Kool G Rap, Kane—I’ve listened to them since day one, I’ve met them, and they’re exceptional MCs. I mean, exceptional MCs. 27 In the old days you always used to argue who was better—Big Daddy Kane, Rakim, or Kool G Rap.
Havoc, Mobb Deep
I learned how to rap just copying from the styles of the artists that was out back then—Big Daddy Kane, Kool G Rap, Rakim, stuff like that. I used to memorize their stuff and try to get a style—like, form a technique —see how their technique was.
I think everyone as a writer who came up in the ’80s was influenced in some way, shape, or form by Rakim—[and] I definitely appreciated Big Daddy Kane, Kool G Rap…. Those were a lot of my early influences.
The four rappers themselves also often mention each other when they talk about influential and innovative rappers of the golden age.
Big Daddy Kane
I come from where you’re hearing cats like Kool G Rap, KRS-One, Rakim—you’re hearing a lot of rappers that’s spitting hard, so it’s like you gotta stay on top of your toes because there’s a lot of competition.
Kool G Rap
Being from the era that I’m from, you had to really stand your ground as far as this lyric shit, and that’s why that era bred rappers like a Big Daddy Kane, a KRS-One, a Rakim…. These dudes, they moved you—they moved you from the soul. Their rapping capability and ability—these dudes were phenomenal.
The Juice Crew guys kept me on my toes. When you hear some hot shit, like what Kane and G Rap was doing back then, you can’t wait to go home and try to top it.
Since the end of the golden age, around 1994, rappers have mostly employed different combinations of the techniques mastered during this time.
That’s not to say that there haven’t been any innovations from 1995 onwards, but the bulk of the development was done during the golden age, hence why the following rappers are so influential. It is difficult to do any rapping without using something that they either pioneered or perfected.
Rakim is often named as the best rapper of all time, based on his monumental impact on the techniques of rapping in 1986. Rappers before Rakim mainly used similar old-school flows—Rakim changed and updated the entire style of rapping, so that the previous style sounded simplistic and outdated. Most rapping recorded after Rakim’s debut in 1986 owes a debt to Rakim.
Kool Moe Dee
I would venture to say that Rakim is the most studied MC ever. Any MC that came after 1986 had to study Rakim just to know what to be able to do. As Michael Jordan is the basketball player’s basketball player, Rakim is the MCs MC.
Rakim changed the “flow” of rapping—the rhythms and the rhyme schemes. His rhythms were more intricate and have been compared to jazz saxophone improvisation, rather than the more sing-songy, basic rhythms of previous rappers.
I ain’t played [the saxophone] in a couple of years, but I think that had a lot to do with my rhyme flow. Playing the sax and then enjoying jazz music, man. It’s like I learned how to find words inside of the beat. The syncopation and the pauses is all from knowing music, playing the saxophone, listening to John Coltrane and Thelonius Monk and the crazy shit they were doing. I just tried to incorporate that into my rhyme flow. That played a big part in my flow.
His rhyme schemes were more complex, rhyming several times inside the bars of music, rather than using one simple rhyme near the end of each bar like most of his predecessors.
I remember when Rakim came out—that was like a big moment. Up until [Rakim], everybody who you heard rhyme, the last word in the sentence was the rhyming [word], the connection word. Then Rakim showed us that you could put rhymes within a rhyme, so you could put more than one word in a line that rhymed together.
Back in the day I would split the paper with two lines down the middle of the paper, which left me with three sections. I would rhyme in all three sections in every bar. So not only was I rhyming at the end, I was rhyming on the first part of the rhyme, the middle part of the rhyme and the second part of the rhyme. Then when the second bar come, the words would rhyme with the first part of the bar before that, and the middle would rhyme with the middle. This is how I started creating different styles and different rhyme forms and shit like that. I’ve done so many joints like that I don’t even have to split the paper any more. It became like just knowing what I had to do. If I spit this on this bar I know what I had to do on the second bar to make it rhyme. That’s how I started creating styles, man, just drawing lines on the paper and putting rhymes in each section.
He also took the delivery (how a rapper uses his/her voice) and the content in different directions as well, using a laid-back conversational tone instead of the louder party voice most rappers had used previously. He focused on witty wordplay and clever uses of language and really put the focus on expanding what could be done with rapping.
Among New York MCs there was no one like Rakim. In Rakim, we recognized a poet and deep thinker, someone who was getting closer to reflecting the truth of our lives in his tone and spirit. His flow was complex and his voice was ill; his vocal cords carried their own reverb, like he’d swallowed an amp. Back in 1986, when other MCs were still doing party rhymes, he was dead serious…. He was approaching rap like literature, like art. And the songs still banged at parties.
I always saw Rakim as a kind of king of the cosmos. A kind of cosmic sound ruler on the same level as an artist like Jimi Hendrix. [Rakim] was unique for his time because of his coolness. With the possible exception of Spoonie Gee, all the other rappers were shouters. In the jazz sense, Louis Armstrong was a shouter and Lester Young and Miles Davis were cool. [Rakim] was cool like that.
It can be hard to appreciate his impact today, as listeners are so used to hearing this more sophisticated type of rapping. To get a sense of the significance of his debut, it can be helpful to listen to some of the earlier rap recordings, such as Sugarhill Gang’s “Rapper’s Delight” and Grandmaster Flash and the Furious Five’s “The Message.”
Imagine how back then all rapping had that similar sound—the sing-songy, party flow with the big, loudly projected voices and sparsely rapped rhythms.
Kool G Rap
If you had any kind of futuristic flow in comparison to the times back then, it probably wouldn’t even be that noticeable now. You’d have to saturate yourself in the music that was going on then to hear the difference.
Then listen to Rakim’s style on “My Melody” (under the group name Eric B. & Rakim)—notice how his delivery is a lot more conversational, and how the rhythms aren’t as easy to predict as those on the old-school songs. Remember that this new style is in the context of there only ever being the simpler style up until this point—this will give insight into how important Rakim is to rapping.
Rakim brought so much new thought and technique to the game when he rhymed, it was like he single-handedly reinvented the art form of being an MC. Rakim was doing for rapping what I had done for DJing; he saw the limits of what was out there and figured he could do more.
Kool G Rap
While Rakim is known for influencing almost everyone after him, either directly or indirectly, Kool G Rap (of the hip-hop collective the Juice Crew) is often noted for specifically influencing the most complex rappers who came after him, due to his intricate style of rhyming.
Kool Moe Dee
Kool G Rap is the progenitor and prototype for Biggie, Jay-Z, Treach [of Naughty By Nature], Nore, Fat Joe, Big Pun, and about twenty-five more hard-core MCs. And if you go back and listen, you’ll see that he’s truly the most lyrical of them all…. He made records for the streets, but because he was so lyrical, only future MCs and lyrical junkies could really appreciate what he was doing. He never chose the commercially musical tracks, or made the types of records that would have gotten him any type of airplay.
Kool G Rap is a major influence. What he did with rapping was he took the lyric level to the highest level it can go. Rakim was scientific, Big Daddy Kane was acrobatic, but Kool G Rap was bloody chainsaws fighting each other lyric style. He took it to a level where it can’t go no further. He took it to the highest level.
One of his main focuses was on continually advancing “compound rhymes,” which are rhymes with more than one syllable, such as “random luck” rhyming with “vans and trucks.”
He gradually made this the main trademark of his flow as he advanced compound rhyming from 1986 through to the mid-1990s. The only thing halting any further advancement of the technique was that by this time all of his bars of lyrics were entirely full with rhyming words, taking it to its inevitable limit.
Kool G Rap
[With] multisyllable rhyming, it’s not like you’re just rhyming fight and then light and then “with all my might.” You’re rapping random luck with handsome fuck, “we cop vans and trucks”—it be shit like that. It ain’t just doing the basics, because that’s not ear catching—[more basic rhymes] don’t catch the ear like that.
Many rappers, such as Jay-Z, Eminem, and Big Pun, pay homage to the work Kool G Rap did during the golden age of hip-hop. Most of the more complex rappers today use compound rhymes, as it is a technique that immediately signals an advanced rapping style.
What I try to do is I try to rhyme two words every bar, it’s a lot harder— you’re actually writing double the rhymes. There’s only a few rappers that really can rap like that, like Kool G Rap.
As well as his influence on rhyming, he was one of the pioneers of more gritty, realistic portrayals of street life, such as on “Streets of New York” in 1990, and introducing Mafioso content into his raps, several years before albums like Raekwon’s Only Built 4 Cuban Linx made Mafioso themes widely popular in 1995. Even when adopting a hard-core, gangster image, the focus was always primarily on the high calibre of rapping rather than on the image, unlike a lot of rappers who followed in his footsteps.
Raekwon, Wu-Tang Clan
When I think about me being in the street all my life and listening to Kool G Rap: “In the streets of New York, dope fiends leaning from morphine,” it was like he was talking to me. It was like he was talking to me personally and talking to the world from our perspective and where we was at.
Kool G Rap
The only [rapper] that came close to being blatant street before me was Melle Mel when he did “The Message,” because that was kinda hardcore right there. But he didn’t run with that style. When I caught it, I ran with it. Right after “Riker’s Island,” I did “Road to the Riches.” The next album I did “Streets of New York.” What’s more blatant than that? And to this day street rap is what rules. Everyone says you gotta make commercial songs, [but] those songs are street commercial songs. All 50 [Cent]’s shit is some street shit, [Jay-Z]’s shit was some street shit, Biggie’s shit was some street shit—they just learned how to do it in a commercial manner. It’s that particular style of rap that rules to this day and in my opinion it’s always gonna rule.
Big Daddy Kane
Another member of the Juice Crew, alongside Kool G Rap, was Big Daddy Kane. Kane made similar advances in rhyme as Kool G Rap during the same period of time (they would often rap over the phone to each other in friendly competition), and he experienced more commercial success—because of this he is generally more widely known than Kool G Rap.
Big Daddy Kane
Me and [Kool] G Rap had a competitive relationship, but it was for the best. It was the type of thing where we’d talk on the phone at night and G would be like, “I got this joint,” and he’d kick it and I’d go, “Aight, I got something.” When we hang up the phone we [were] like, “Damn, he came hard,” and we [went] back to the pen and paper. We always had love for each other. For me there was always a certain way I felt about G —I always feel like I took his slot. I always felt he never got the props he deserved. When I took off it wasn’t really room for two, so my man never got to shine the way I know he could have. I don’t think the world really knows how great [Kool G Rap] is on the mic.
Big Daddy Kane was one of the first rappers to introduce the smooth, ladies’ man persona, though with an emphasis on the rapping technique first and the image second. He mixed this with witty battle-rap punchlines and a sarcastic, condescending tone. His vocal delivery is also one of the most revered in hip- hop—a smooth baritone comparable to Rakim’s.
[Big Daddy] Kane was playing a role, hip-hop’s first playboy: He had the silk robes and pretty girls in all his videos, all that. But his flow was sick…. He was condensing, stacking rhymes one on top of another. Trying to keep up with him was an exercise in breath control, in wordplay, in speed and imagination. He was relentless on the mic.
RZA, Wu-Tang Clan
Big Daddy Kane was one of the first MCs with swagger. This dude had the Brooklyn aggressiveness and yet he still has all the girls on him and he still had hardcore styles.
Kane is often placed in lists of the top five rappers ever, as he is one of the most studied lyricists of the golden age—named by many of the next generation as an artist whose records taught them how to rap. Also noteworthy is his ghostwriting for other artists, such as Biz Markie and Roxanne Shanté, and his versatility in being able to write in different styles to suit their personas.
To me, Big Daddy Kane is still today one of the best rappers. I would put Big Daddy Kane against any rapper in a battle. Jay-Z, Nas, Eminem, any of them. I could take [his song] “Raw” right now and put it up against any record [from today]. Kane is one of the most incredible lyricists … Big Daddy Kane can rap circles around cats.
KRS-One, formerly of the group Boogie Down Productions, is known as an incredible live MC, with the levels of outstanding enunciation, timing, vocal presence, and energy needed for live performance.
O.C., Diggin’ in the Crates
Probably the first thing I learned in MCing is breath control, I learned that from KRS. I seen him do a show one time—I seen him rock for two hours that night. He had his hype man or whatever, but for the most part I never seen nothing like that. Like, damn, this dude sounds like his records or better.
On his records, his subject matter often aims to educate listeners, introducing them to political and historical issues and events, as well as the promotion of socially aware hip-hop in general.
KRS was also telling people things nobody else did: don’t smoke crack, stop making babies, stop committing black-on-black violence … know your history. It all seemed so obvious, but it took on a new meaning coming through the speakerbox on the radio. Now the Bronx had a rapper who told it like it was. KRS wasn’t a braggart about anything other than the knowledge he had to teach.
Through his flow, he helped to introduce a lot of new varied rhythms, sometimes borrowed from reggae and ragga MCing. His records are often exciting and unpredictable to listen to because of this, with numerous changes in the flow throughout his songs—this paved the way for later rappers with rapid-fire, alternating flows, such as the groups Das EFX and Fu-Schnickens.
Kool Moe Dee
[KRS-One] is one of the more versatile MCs in the game. I think he has more styles than anybody, period … [he has] more flows than anybody I have ever heard.
KRS-One is also known as one of the premier battle rappers, due to his live performance skills, his ability to improvise lyrics off the top of his head, and his knowledge of a wide array of rapping styles.
[KRS-One] was dropping knowledge and it was still hard. That’s incredibly hard to do: to get accepted, to get your point across and be looked at like an incredible lyricist and stage performer. He covered everything. His stage show is crazy, freestyle is crazy. He can get deep on you. His battle raps are crazy. He was the teacher. He was dangerous.