In part 2 of the 50 greatest rappers of all time, Stop The Breaks looked at a range of rappers, including The Fresh Prince, The D.O.C., CL Smooth, Sticky Fingaz, Canibus, Raekwon the Chef, Biz Markie, Big L, Prodigy and AZ, and what made them the best to ever do it.

So here we go, Stop The Breaks looks at part 3, the top 30 to 21 of the 50 greatest rappers of all time.

30. Treach – Greatest Rappers Of All Time

 Discography: The Independent Leaders (as The New Style) (1989), Naughty by Nature (as Naughty by Nature) (1991), 19 Naughty III (as Naughty by Nature) (1993), Poverty’s Paradise (as Naughty by Nature) (1995), Nineteen Naughty Nine: Nature’s Fury (as Naughty by Nature) (1999), IIcons (as Naughty by Nature) (2002), Anthem Inc. (as Naughty by Nature) (2011)

Treach is the very definition of a rapper’s rapper. Revered by Eminem and a close friend of 2Pac’s, Treach may not get the mainstream recognition he deserves but on the low, he might be one of the most influential rappers of all time.

The street-radio formula used by so many rappers these days, from Jay-Z to 50 Cent to Rick Ross, was perfected by Treach in the early ‘90s during Naughty by Nature’s ridiculous run. Straight off the bat, the group launched into superstardom on the strength of “O.P.P.” and reached a new level with “Hip Hop Hooray” – two of the greatest hip-hop singles of all time.

Very few hip-hop artists manage to consistently appeal to both the streets and the radio. Naughty by Nature achieved this like it was second nature to them and in a big part, it was due to Treach’s incredible rhyme skills and knack for writing big, catchy hooks.

29. Q-Tip – Greatest Rappers Of All Time

Discography: People’s Instinctive Travels and the Paths of Rhythm (with A Tribe Called Quest) (1990), The Low End Theory (with A Tribe Called Quest) (1991), Midnight Marauders (with A Tribe Called Quest) (1993), Beats, Rhymes and Life (with A Tribe Called Quest) (1996), The Love Movement (with A Tribe Called Quest) (1998), Amplified (1999), The Renaissance (2008), Kamaal/The Abstract (2009)

Q-Tip is one of the few rappers-producers who manages to be at the top for both crafts. With his production work on all of the A Tribe Called Quest albums as well as for Nas and Mobb Deep, Tip secured his legacy as one of the greatest hip-hop producers of all time.

But as far as rapping goes, not enough hip-hop fans give Tip the props he deserves. As one of the most unique voices in the rap game – sonically as well as content-wise – Tip subtly changed the hip-hop landscape, moving from the aggressive, battle raps of the pioneers to a more conversational style.

This opened up rapping styles to include more emotion, different rhymes and unique flows for later artists – everyone from Nas to Kanye has been inspired by Q-Tip. Even after the demise of A Tribe Called Quest, Tip pushed forward and managed to drop a couple solo albums, including the classic 2008 album, The Renaissance, which showcased Tip bringing back the Tribe vibe to the modern era.

28. Talib Kweli – Greatest Rappers Of All Time

Discography: Mos Def & Talib Kweli are Black Star (with Mos Def as Black Star) (1998), Train of Thought (with Hi-Tek as Reflection Eternal) (2000), Quality (2002), The Beautiful Struggle (2004), Liberation (with Madlib) (2007), Eardrum (2007), Revolutions Per Minute (with Hi-Tek as Reflection Eternal) (2010), Gutter Rainbows (2011), Prisoner of Conscious (2013), Gravitas (2013)

At the young age of 24 and on his debut album , Talib Kweli’s rhymes were drenched in social conscious, politically aware, black teachings; his flow was nimble; delivery razor sharp and enunciation pristine.

As an rapper Kweli can be quite the paradox. His lyrics bask in sunny optimism; he celebrates his life; his love for Brooklyn, his music, his culture and hip hop.

Yet on the flipside, in the battling sense, Talib is simply world class. Attacking the mic with relentlessness, he rhymes with unlimited energy and vigour, earning his spot as one of the greatest rappers of all time a long time ago.

27. Lauryn Hill – Greatest Rappers Of All Time

Discography: Blunted on Reality (as The Fugees) (1994), The Score (as The Fugees) (1996), The Miseducation of Lauryn Hill (1998)

Aside from MC Lyte, Lauryn Hill is the only other female rapper to appear on my list and to be placed above lyrical heavyweights like Pun, L and Royce probably means she’s not too bad a rapper right? Well that’s quite an understatement.

Lauryn Hill’s incredible rhyme skills would enable her to rip apart any naysayers who think she’s soft – impeccable flow, on-point delivery and pristine enunciation make her a lyrical champ.

And it’s her voice that makes her such a dangerous rapper – able to croon as softly as a jazz musician but when spitting hot verses it cuts straight through the listener’s ear.

Lauryn Hill’s main strength, though, lies in her songwriting. Her lyrics are simply pure poetry in motion, her rhymes transcend across a range of raw emotions and because she’s such an accomplished singer, she knows how to craft the perfect hook.

The Miseducation of Lauryn Hill was more than just a hip hop record; it embraced a wide range of musical forms and genres, demonstrating Lauryn Hill’s amazing capabilities as a hip hop artist.

26. Kanye West – Greatest Rappers Of All Time

Discography: The College Dropout (2004), Late Registration (2005), Graduation (2007), 808s & Heartbreak (2008), My Beautiful Dark Twisted Fantasy (2010), Watch the Throne (with Jay-Z) (2011), Cruel Summer (2012) (with GOOD Music), Yeezus (2013)

Every year since 2007, Kanye West has consistently been one of the best rappers alive. In 2007 he stepped up to a new level, rapping-wise, dropping his first street anthem with “Can’t Tell Me Nothing” and bodying Lil Wayne on “Barry Bonds.” In 2008 he put out 808s & Heartbreak but still found time to rip through joints like “Lollipop (Remix),” “Put On,” “Swagga Like Us” and “Go Hard.”

2009 was all about the feature appearances – Ye went on a guest verse bodying tour, killing shit like “Kinda Like a Big Deal,” “Run This Town” and “Forever.” 2010 and 2011 were My Beautiful Dark Twisted Fantasy and Watch the Throne. Enough said. 2012 was Cruel Summer and his epic verse on Rihanna’s “Diamonds (Remix).” Last year, he dropped Yeezus and is on his way to change the game yet again.

My point is, Kanye is often looked to as one of the greatest and most influential hip-hop artists in the past 10 years but people often sleep on him as a rapper. Which is kinda crazy to me. Who else can go line for line with Jay-Z on an entire album and not get completely overshadowed? Who else can maintain best rapper alive status for 7 years straight? Who else can shift the hip-hop landscape with the drop of an album?

Old school traditionalists can argue all they want but the evidence is all there – Kanye West is unarguably one of the greatest rappers of all time.

25. Big Pun – Greatest Rappers Of All Time

Discography: Capital Punishment (1998), Yeeeah Baby (2000), Endangered Species (2001)

Big Pun is simply a super-duper-magnificent lyricist. The way he conjures words up and makes them rhyme together, it’s astounding to listen to.

In terms of rhyming prowess then there’s no denying – Pun was the heavyweight champion in that arena. But it wasn’t just his lyrical skills; his debut album Capital Punishment was the first album by a Latino rapper to go platinum and despite his hardcore, street image – the track ‘Still Not a Player’ became a hit and was also Pun’s most successful single released.

So with his extra-extraordinary lyrical abilities and influence on upcoming Latino rappers, Big Pun is definitely one of the greatest rappers of all time.

24. GZA – Greatest Rappers Of All Time

Discography: Enter the Wu-Tang (36 Chambers) (with Wu-Tang Clan) (1993), Wu-Tang Forever (with Wu-Tang Clan) (1997), The W (with Wu-Tang Clan) (2000), Iron Flag (with Wu-Tang Clan) (2001), 8 Diagrams (with Wu-Tang Clan), Words from the Genius (1991), Liquid Swords (1995), Beneath the Surface (1999), Legend of the Liquid Sword (2002), Grandmasters (with DJ Muggs) (2005), Pro Tools (2008)

If Kool Moe Dee touted Pharoahe Monch as a linguistics professor than I’ll make the claim right now that GZA is head of the literature department.

Capable of mind-dazzling wordplay, GZA is a master of the less-is-more approach, combining sinister imagery with a brutally efficient lyrical style. However, despite the concise rhyme technique he employs, GZA is surprisingly a very effective storyteller.

Take ‘Exploitation of Mistakes’ for example. One of the most chillingly, cold-hearted narration of murder ever lain to wax, it’s so great because of GZA’s attention to detail – note the inclusion of obscure elements to the crime scene; the position of the body, identifying features, DNA samples. Simply brilliant.

To this day Liquid Swords not only remains the most formidable challenge to Only Built 4 Cuban Linx… as Wu-Tang’s greatest solo but also as one of the tightest, most intricately crafted hip hop albums of all time.



23. Mos Def – Greatest Rappers Of All Time

Discography: Mos Def & Talib Kweli are Black Star (1998) (with Talib Kweli as Black Star), Black on Both Sides (1999), The New Danger (2004), True Magic (2006), The Ecstatic (2009)

A deep, poetic lyricist coupled with one of the nimblest flows in hip hop, Mos Def, like his close friend Talib Kweli, combines pure rhyming skills with intelligent thoughts to the highest level.

The funny thing about him is that, despite his near-veteran status in the industry, Mos Def rhymes with that same vigour and energy like he did back in ’98 when he debuted.

Despite an erratic output of albums, Mos Def had continually strived to expand his artistry beyond simply rhymes and beats – his sophomore album The New Danger incorporated jazz grooves, rock influences and blues-inspired jam sessions, and though it was hailed as a sprawling mess, it showed Mos Def had guts and vision.

However, when he’s completely focused then Mos Def is simply a tour-de-force, lyrical and album-quality-wise, as shown recently in The Ecstatic. Socially conscious and with a well of endless creativity, Mos Def remains one of hip hop’s most quirky and talented rappers of all time.

22. Busta Rhymes – Greatest Rappers Of All Time

Discography: The Coming (1996), When Disaster Strikes… (1997), E.L.E. (Extinction Level Event): The Final World Front (1998), Anarchy (2000), Genesis (2001), It Ain’t Safe No More… (2002), The Big Bang (2006), Back on My B.S. (2009), Year of the Dragon (2012)

Although fans of KRS-One, The Roots, and Chuck D may say otherwise, I think Busta Rhymes may be hip hop’s greatest live performer. Full of invigorating flair and fun-packed energy, Busta Rhymes not only performs well onstage but manages to bring that showmanship onto the record.

That’s why artists ranging from The Pussycat Dolls to DMX; Nas to Gym Class Heroes; A Tribe Called Quest to Asher Roth have all called upon Busta Rhymes for some of that “RRRRRROAW RRRRRRROAW” liveliness.

While The Coming debuted in 1996, Busta Rhymes had already put out a couple of albums with Leaders of the New School; making him one of the few relevant Golden Age rappers still putting out decent albums. From 1991 to 2009, 18 years in the game and he’s still tearing up guest appearances and demolishing the stage.

21. Big Boi – Greatest Rappers Of All Time

Discography: Southernplayalisticadillacmuzik (with André 3000 as Outkast) (1994), ATLiens (with André 3000 as Outkast) (1996), Aquemini (with André 3000 as Outkast) (1998), Stankonia (with André 3000 as Outkast) (2000), Speakerboxxx/The Love Below (with André 3000 as Outkast) (2003), Idlewild (with André 3000 as Outkast) (2006), Sir Lucious Left Foot: The Son of Chico Dusty (2010), Vicious Lies and Dangerous Rumors (2012)

One of the worse things a hip-hop fan can do is sleep on Big Boi in favour of Andre 3000. I can see why it happens though. Andre is just on a different level to any other artists – from his look to his ideas to his voice to his rhymes – 3 Stacks is a one-of-a-kind in this rap shit.

That’s why it was so important to have Big Boi as the other half of OutKast. If Andre 3000 was the alien taking listeners to out of space then Daddy Fat Sax was the pimp hustler bringing them back down to Earth to smoke some chronic.

OutKast fans also have to thank Big Boi. While Andre was off doing his TV shows and Gillette commercials, Big Boi put in the work to keep the OutKast flag up and dropped two incredibly dope solo albums – Sir Lucious Left Foot: The Son of Chico Dusty and Vicious Lies and Dangerous Rumors.

Very few rappers these days can keep up with Andre 3000 over the entirety of one record. Big Boi not only kept up with him over 4 albums, there were times where he had the better verse! It’s understandable that we think of Stacks as the better rapper out of the two, just don’t forget that Big Boi is also one of the greatest rappers of all time.

More in the 50 Greatest Rappers Of All Time series:

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Written by Hao Nguyen
Stop The Breaks is an independent music marketing company focused on showcasing independent hip-hop artists. Our goal is to help motivate, inspire and educate independent artists grinding around the world. We provide branding, content marketing, social media, SEO and music promotion services.