The Best of the Best: The 50 Greatest Emcees/Rappers Ever (#20-11)

Aug 23 '04 (Updated Aug 07 '08)    Write an essay on this topic.


The Bottom Line Booyah!

Having reached the Top 20, the "Greatest Emcees Ever" list gets down to the true heavyweights. Each and every cat from now on in is legendary in their own way, by default. The influx of the New School slightly wanes to let in some of the pioneers, the old school... let's get it moving with numbers #20-11...


#20. Big Punisher.

The first and last Latino emcee on my list, I don’t really need to search hard to explain why Big Pun’s here. He has a similar quality to Pharoahe Monch, which is when you listen to the now-deceased, larger than life rapper you simply run out of superlatives. Breathtaking, frantic, complex, witty, hilarious… Pun had delivery and flow in abundance, charisma and guile for years, and a canny ability to create stunning songs about anything he wanted. He could also crossover without losing any artistic integrity whatsoever and that’s the rarest of skills, something which propelled him to near-superstar status. Anyone who’s heard his classic album Capital Punishment will know that, to be honest, I am privileged to have heard Pun spit. It’s just a shame his weight problems caused his untimely death.

Essential Listening: "Capital Punishment" (1998), “Yeeeeah Baby” (2000).


#19. Del Tha Funky Homosapien.

One of the most integral members of the Westcoast underground, the veteran Bay Area rapper is yet another choice on this list that may surprise some. So why do I pick Del? First and foremost, the cousin of Ice Cube is a surprisingly nimble, dexterous lyricist with a vivid imagination and a talent for ploughing this imagination into fantastic lyrics. Secondly, along with his classic solo debut “I Wish My Brother George Was Here” and the recent, far-out extravaganza “Deltron 3030” Del’s discography is fantastic. And lastly, he is the driving force behind the literate, classy Oakland-influenced underground that spawned a number of talented artists; Del got behind this as a staple of the Souls of Mischief and the Hieroglyphics crew. A pioneer in the rap game, Del is also so slept-on it’s not funny, and more than deserves his spot.


#18. Lord Finesse.

Self-proclaimed leader of the Diggin’ in the Crates crew, old school emcee extraordinare Lord Finesse gets few proper props from few heads. Finesse – along with Big Daddy Kane – essentially fathered the witty, punchline-fuelled style that cats like Big L, Chino XL and later Eminem would go on to make a career out of. “Funky Technician” exploded out in 92, a magnificent throwback to the old school, with verse after verse of unrestricted, relentless wordplay and humour crammed rhymes delivered charismatically by Finesse. This fantastic style became a massive hit with the rap crowd, and throughout the 90s the veteran rapper never fell off, eventually moving into production (Finesse’s most famous track to the unenlightened is surely “The Message”, from Dr. Dre's 2001). Finesse has had more impact and influence that your favourite rapper, it’s that simple.

Essential Listening: “Funky Technician” (1992), “The Awakening” (1996)


#17. Masta Ace.

I’ll admit, before 2001’s classic “Disposable Arts” I had never heard of Masta Ace, bar his verse on the celebrated posse cut The Symphony. However, since that moment - and having explored his past releases – it has become startlingly clear to me that the influence, talent and general impact that Ace has had on the Eastcoast underground is near-unparalleled. Dropping a number of dope, strictly underground LPs at the tail end of the 80s and during rap’s “Golden Era” – either solo or as part of Masta Ace Incorporated – after a long hiatus he surfaced again in the new millennium with the aforementioned album. Displaying all the talents that first endeared him to the public, Ace represents any “realness” there is left in the game. A frank, clear spitter who embraces creativity and originality, Ace revels in criticising the state of the current rap scene, and yet again blew away everyone with this year’s best album A Long Hot Summer.

Essential Listening: “Take a Look Around” (1990), “Sittin’ on Chrome” (1993), “Disposable Arts” (2001).


#16. Slick Rick.

Everyone loves a good story. And that’s why Slick Rick is a legend in this here rap game. Born around my patch, in London, England, his 1989 breakout classic album “The Great Adventures of Slick Rick” was the ultimate demonstration in storytelling rap. Suspense, narratives, character development... Ricky had it all – and this is leaving out his fluid, smooth style that essentially fathered Snoop Dogg's whole steez. Think of the great storytelling emcees of the 90s – Ice Cube, Nas, O.C., Biggie – and you can trace one of their characteristics back to Slick Rick. Never one to shirk controversy, Slick has had various problems shadowing his every move in his career, but in many ways that adds to his legacy. For better or worse, with the eye patch and gold chains, Slick was truly the beginning of the Pimp movement.

Essential Listening: “The Great Adventures of Slick Rick” (1989), “The Rulers Back” (1991)


#15. Pharoahe Monch.

I know this rhetoric might be redundant by now - having enthused over Bis, Aceyalone and Pun - but listening to the Queens emcee spit is an experience that makes you realise why hip hop is so great. As part of legendary duo Organised Konfusion, the early 90s found the uber-talented Monch obliterating each and every single verse he dropped. The master of breath control, with an out-of-control flow and enchanting delivery, Monch delivers complex, layered lyrics at the speed of light – I have to yet to hear a rap fan criticise him. A series of fine albums with his also-talented partner Prince Po, plus a very good solo effort, meant that the fantastic talent of Monch has largely been exploited, which is very important. How many artists on this list have not had this luxury? While not as active recently, a move to Dr. Dre's Aftermath Entertainment will hopefully see another outstanding solo effort dropping.

Essential Listening: “Organised Konfusion (1991), “Stress: the Extinction Agenda” (1994), “Internal Affairs”" (1999)


#14. Big Daddy Kane.

As I’ve mentioned before, Big Daddy Kane is the father of so many emcees’ styles on this list it’s not even funny. The staunchly old school emcee specialised in battle rhymes and braggadocio– a scything, wordplay and insult-infused style of rap that is the fundamental centre of rap culture – and he was the first to bring it to the masses in a big way. Add the humour, the tongue-in-cheek misogyny, and the confidence and there was formed a remarkable, hugely talented rapper. And his catalogue – while sometimes underwhelming – largely reflected this fact. Long Live the Kane and It’s a Big Daddy Thing demonstrated the flawless, peerless (at the time) technique of Big Daddy. Ok, occasionally he can sound simplistic compared to the highly advanced, futuristic rhyme schemes of the 90s finest, but that goes for virtually any other old school artist on this list.

Essential Listening: "Long Live the Kane" (1988), "Its a Big Daddy Thing" (1989)


#13. Gza.

The Wu-Tang Clan’s influence on my list finally comes to an end, with their head emcee and lyrical epicentre, Gza. Representing everything that is good about complexity in the art of emceeing, the “Genius” as he is commonly known is undoubtedly the finest exponent of wordplay there is. Quite literally standing out on every single Wu-Tang Clan album there has ever been, the package includes a deceptively skilful flow, a fantastic voice and pin-point sharp, razor-blade lyrics encompassing obscure metaphors, wonderful double meanings and literary devices the dictionary couldn’t define. His frankly masterpiece solo debut “Liquid Swords” is the second best Wu-Tang solo of all time – quite a compliment – and a number of other solid albums that followed simply backed up that legacy. Unlike the vast majority of this list, at no point in his career has Gza fallen off and he has stayed at the same stratospheric levels of consistency.

Essential Listening: “Liquid Swords” (1995), “Beneath the Surface” (1999)


#12. Kool G Rap .

The master of crime rap throughout the 80s and 90s, the NYC legend packs one of the most fearsome flows in the rap game and has gained a considerable fanbase with it. With a distinctive voice and lisp that belies his intelligent, street-smart philosophising, G Rap first sprung to attention in the mid 1980s with his partner DJ Polo and as a member of the legendary Juice Crew. The various albums that followed – either as a duo or solo – demonstrated all the attributes that made the “Kool Genius of Rap” such a vivid listen. Reality-drenched, pacy storytelling describing in thorough detail the underworld of New York - over dark, sombre production from greats such as Marley Marl, Sir Jinx and Large Professor – this is G-Rap’s formula, and he’s used it time and time again to legendary effect.

Essential Listening: “Road to the Riches” (1989), “Wanted: Dead or Alive” (1990), ׂ,5,6” (1995).


#11. Jay-Z.

Ah yes, the emcee that you either love or hate. It’s undeniable that Jay-Z is a fantastically talented artist: 1995 debut Reasonable Doubt was a wonderful, gritty Mafioso-inspired trip through the “world of a hustler”. It’s also undeniable that Jay is a smart guy and businessman, for he has become one of the most successful rap artists of all time, being able to crossover seemingly at will. And that’s where the problem comes in; while his work ethic of one album a year may suggest otherwise, Jay is a lazy so and so. Too many half-arsed albums have come out under the moniker Jay-Z – which is a shame. Witty, confident wordplay and a fabulously versatile, slippery flow are his trademarks – not forgetting the trademark arrogance – and he could in the Top 5 of this list, but frankly, he doesn’t deserve to be.

Essential Listening: “Reasonable Doubt” (1995), “The Blueprint” (2001), "The Black Album" (2003)

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Previous Installments:

The Greatest Emcees of All Time: #50-41

The Greatest Emcees of All Time: #40-31

The Greatest Emcees of All Time: #30-21


The Greatest Emcees of All Time: #10-1

go get 'em!

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