The Best of the Best: The 50 Greatest Emcees/Rappers Ever (#30-21)

Aug 21, 2004 (Updated Aug 7, 2008)

The Bottom Line We reach the Top 30...

Having got the “contenders” out of the way, here come the Super Heavyweights. As we move into the Top 30 the artists get more and more heavyweight. You’ll notice this is largely Eastcoast dominated, with a couple of Southern/Mid-Western outsiders crashing the party… but what’s really significant is this is the era of the true New School. Virtually all these rappers made it in the 90s, and have been the face of mainstream hip hop in the past few years, so in a few years time expect most of these cats to be right there in the Top 15 or 20. Let’s carry on with 30 - 21...

30. Lauryn Hill.

L-Boogie? A female emcee? At number 30? What the fu*k am I talking about, I’m sure you’re thinking. Well, lose that thought sucka, her verses on The Fugee’s “Score” and “The Miseducation of…” are better than most rapper’s careers. Straight up, the integral, outstandingly talented Fugees mainstay is one of the most scything yet poetic rappers out there. Perhaps more famed for her writing and singing ability, she absolutely blew away Wyclef and Pras on The Score - a misnomer perhaps because my mum could blow them away rapping – but the impression certainly stuck. Clarity, diction, Lauryn Hill can dominate a verse like she probably dominates men. The best female rapper ever, argument ended, only Lady of Rage can come close.

Essential Listening: “The Score” (1996), “The Miseducation of Lauryn Hill” (1998)

#29. Ghostface Killah.

The third of four Wu-Tang Clan members on the list, Ghostface Killah has had the best and most successful solo career out of any of the Wu posse. With two classic albums, “Supreme Clientele” and “Ironman”, Ghost demonstrated excellently his fantastically unique style. Using difficult, complex slang with abstract turns of phrase and a weaving, fast-paced delivery, Ghost is one of the most difficult emcees in the entire hip hop world, to actually fully understand. But his highly accessible flow – so easy to nod your head to – and his absolutely superior ear for outstanding beat selection, means he is a highly experienced, popular and talented pick for #29.

Essential Listening: “Ironman” (1996), “Supreme Clientele”" (2000).

#28. Andre 3000.

I am by no means a fan of the South’s biggest and best group Outkast, but Andre 3000 is one of the main reasons I still listen to their records. Actually that’s a lie, as Dre is more interested in singing than he is rapping now… but back in the day the eccentric, fluid and layered raps of the Outkast frontman established him as one of the top tier emcees in the entire rap game. I still don’t see how people preferred his partner Big Boi – a skilled but fairly conventional rapper – to the highly abstract, elite skills of Andre. Regardless, his ability has driven any interest I have had in Outkast. Just stop singing – it’s not that I’m narrow-minded, far from it, but let’s face it Andre your singing sucks!

Essential Listening: “Atliens” (1996), “Aquemeni” (1998)

#27. Canibus.

Now we stumble onto THE most naturally gifted rapper on this list. Canibus is every hardcore rap purist’s favourite emcee (every epinions hip hop writer here loves him) for a reason, as the gravely voiced, razor-tongued battle specialist has the largest vocabulary in hip hop, a penchant for absolutely killer wordplay, and a stamina that allows him to rhyme for minutes on end. Ever since his infamous beef with LL Cool J and outstanding appearances on tracks by the Lost Boyz and The Firm, Bis has released a number of albums, some good, some disappointing, and has remained staunchly underground. When he makes his masterpiece, expect him to be a strong challenger for the Top 20.

Essential Listening: "2000 B.C." (1999), “Rip the Jacker” (2003).

#26. Eminem.

Ok so the white press will place Em in the Top 10, but in reality he’s not close. We all know about “The Great White Hope” so there’s no need to describe him too much; though shock, controversy and a fair amount of talent Em stormed to critical and commercial acclaim in the late 90s. Backed by production from Dr. Dre, aided by a biting, fantastic talent for witty, satirical rhymes and a creative ability that puts most others to shame, Em’s two acclaimed, if deeply overrated, opening albums gave him massive power. But as the noughties have proceeded, Em has fallen off, to be blunt. Changing his mentality to that of a thug – no doubt thanks to the influence of 50 Cent – and leaping into production (a skill which he has questionable talent in) all we hear now are mediocre verses that don’t bode well for his upcoming fourth album. He’s slipping on this list as we speak…

Essential Listening: “Slim Shady LP” (1999), “Marshall Mathers LP” (2000).

#25. Redman.

The Funk Doctor is quite simply one of the most consistent artists in the rap game; there’s no real better way to describe Redman. Unlike his sometimes-partner Method Man, virtually every release he’s dropped has been stellar (with the exception of the highly disappointing “Malpractice”), and the crazy wordplay and stupendous voice of Red means he has a secure legacy and a large, dedicated fanbase. Unfortunately, recent broadening out has led to accusations of falling off - though his appearance on Christina Aguilera’s “Dirrty” and a popular Pink single won’t have harmed his popularity. But still, Redman is like a more prolific and productive version of Busta Rymes (see #37), which gets him mad props from me.

Essential Listening: “Whut? Thee Album” (1992), "Dare Iz a Darkside" (1994), “Muddy Waters” (1996).

#24. Ras Kass.

In my eyes, Ras Kass is unquestionably the finest lyrical lyricist of the modern rap generation. No other artist – bar Common – can match his sheer ability with words. He has made a career of poetic, vicious rhyming sprees that exude wit, charisma and confidence all at the same time. Soul on Ice, his masterpiece solo album, is the best example of this in rap history… the trouble you might have finding it is tantamount to the flawed genius image of Ras. Controversial with his views on the Government, race and history, as well as someone who has severe scrapes with major labels and the law, Ras is an enigma whose potential has remained largely untapped. What’s been exposed is more than enough to propel him high, high up.

Essential Listening: “Soul on Ice” (1996), "Van Gogh" (2000)

#23. Talib Kweli.

Some find it hard to like Talib Kweli, with a voice that at the best of times sounds like a cross between a 10 year old girl and Dru Down on helium, he can be very difficult to start listening to. Cross this line and you’ll find one of the key members of the late 90s Conscious movement, a highly accomplished rapper capable of high level socio-political commentary, thoughtful introspective questioning, and vicious battle capabilities. Kweli has also been involved with two of the best albums to have emerged in recent times, the project “Blackstar” with fellow cohort Mos Def, and the equally classic “Train of Thought”. Add a near-classic solo album Quality and we’re talking about a true pioneer in the New School movement.

Essential Listening: "Mos Def & Talib Kweli are... Blackstar" (1998), "Train of Thought" (2000), "Quality" (2002)

#22. Black Thought

While most rappers spit their rhymes over relatively basic, bass-driven beats designed to give emphasis and support lyrics, Black Thought is even more impressive by the fact he spits over full-blown musical pieces created by his legendary group The Roots. And how he spits; one of the best battle rappers of his generation, the chemistry between Black Thought and partner Malik B carried the group through a succession of classic releases. Don’t mistake him for a fully conscious emcee – while Thought has more than his fair share of progressive moments, for the most part he sticks to ripping tracks to shreds. And that sounds good to me.

Essential Listening: Do You Want More?!!!??!(1995), Iladelph Halflife (1996), Things Fall Apart (1999), Game Theory (2006)

#21. Mos Def

In a section dominated by New School artists, we come to its leader. Mos Def is one of the most revolutionary artists around – along with the aforementioned Talib Kweli he provided half the impetus for the “Blackstar” project, an album that many rate as a Top 10 rap album ever. What makes Mos special? Intelligence, lyrical fluidity and craft, and just a dope, quirky voice you can’t help warm to. “Black on Both Sides”, his exceptional solo debut, demonstrated all this and more. I mean, who else would write a poignant ode and plea about the lack of water in the Third World? My main beef with Mos is simple; he just doesn’t drop enough. More concerned with his rock band and his acting career, Mos is just not active enough. It’s a damn shame to be honest; but fortunately he’s on his way back with a solo album, coming very soon. Look out for it, I’ implore you.

Essential Listening: “Mos Def and Talib Kweli are… Blackstar” (1998), “Black on Both Sides” (1999)

Previous Installments:
The Greatest Emcees of All Time: #50-41

The Greatest Emcees of All Time: #40-31

The Greatest Emcees of All Time: #20-11

The Greatest Emcees of All Time: #10-1

Check 'em out!

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