Are you Benny or Teddy?

Round of 64 (continued)

Region A

(1) Biggie over (16) Biz markie

The Teflon Don with his precise lyricism, vivid story-telling and powerful voice over-matches Biz Markie’s fun and quirky content and style.

(7) Eric B and Rakim over (10) Heavy D

These two heavyweaights from the 80’s square off in a close battle and the combination of Rakim’s laid-back, laser-like lyricism with Eric B’s mastery of dj’ing and production give the duo the edge over the fun, dance-friendly rap style of Heavy D.

(9) DMX over (8) Bone Thugs ‘n Harmony

A battle of 90’s titans, DMX edges out Bone Thugs despite their 1997 Grammy for “Crossroads”.  At his peak in the late in 90’s, DMX was the top dog in hip-hop, a chip Bone Thugs can’t boast.

(5) BustaRhymes  over (12) Dj Jazzy Jeff and the Fresh Prince

Busta’s high-energy stage presence and colorful persona, is too much for the trail-blazing, clean-cut duo of DJ Jazzy Jeff and the Fresh Prince.  Parents Just Don’t Understand that Busta’s Got You All in Check.

(4) Will Smith over (13) Gangstarr

Though brilliant together, the sharp flow of Guru and the master production of DJ Premier are no match for the four-time Grammy-winning MC who never swears.

(3) Beastie Boys over (14) Fat Boys

Though their music was both fun and funky and their presence in the 80’s cannot be overstated, paving the way for heavy-set emcee’s as an acceptable hip-hop image, the Fat Boys don’t have enough in the tank to outlast the legendary Beastie Boys whose run of hits spanned an 8-year peak with 7 award-winning platinum albums between 1986-1994.  These Boys have a License to Ill indeed.

(2) Snoop Dogg over (15) Pete Rock and CL Smooth

Though not yet a Grammy winner, the Doggfather’s 16 nominations between 1994-2013 speak to Snoop’s consistency and ability to stay relevant in hip-hop’s ever-changing landscape.  This is where Pete rock and CL Smooth fall short as they started strong from 1991-1994, disbanded for 15 years, and haven’t yet regained their early notoriety since their reunion in 2010.


Region B

(1) Eminem over (16) Foxy Brown

Foxy’s critically-acclaimed work and sex appeal fall short of matching up with Slim Shady’s lyrical excellence and slew of multi-platinum albums.

(15) Mos Def over (2) Sugarhill Gang

In a stunner, Mos Def’s superior lyricism, eclectic content and inspired beats proved too much for the old-school powerhouse, despite their ground-breaking impact.

(3) Missy Elliot over (14) De La Soul

In a match that was closer than the 3-14 seeding, Missy squeaks by De La’s creativity and consciousness on the strength of her consistency and uniqueness.

(4) Big Pun over (13) Common

The beast from the Bronx carries Puerto Rico on his back as he edges out one of Chicago’s finest in Common.

(5) Big Daddy Kane over (12) Kurtis Blow

The smooth operator’s lyrical dominance over Kurtis Blow gives him the edge in this battle of 80’s standouts.

(6) Ludacris over (11) E-40

In a match-up between two of the more unique and up-tempo rhyme styles in our bracket, Luda’s commercial success, including three Grammy’s, earn him the victory.

(7) Talib Kweli over (10) Grandmaster Flash and the Furious Five

In a ‘student beats the teacher’ match-up, the carefully-crafted, rapid-fire, conscious rhymes of Talib Kweli narrowly beat out his socially-aware 80’s counterparts.


Region C

(1) Jay-Z over (16) MC Hammer

Despite greatly elevating hip-hop’s commercial appeal in the early 90’s, the ‘U Can’t Touch This’ star’s pop-friendly sound and James Brown-esque dance moves were no match for Jay-Z’s superior lyrical ability and expansive catalog of hits.

(2) Run-DMC over (15) Ice-T

It’s Tricky to rock a rhyme, but in the 80’s and early 90’s Run-DMC mastered the craft and as such overmatch Ice-T’s influence on elevating gangsta rap.

(3) Nas over (14) Cypress Hill

God’s Son’s vast catalog of critically-acclaimed tracks and albums combined with his place amongst the best lyricists of all time prove too much for Cypress Hill, despite their heavy, largely pot-smoking cult following.

(4) LL Cool J over (13) The Roots

A close match-up despite LL’s heavy edge in the seeding, Mr. Smith pulls out a victory over the Legendary Roots Crew on the strength of his ground-breaking impact as hip-hop’s first solo icon and his ability to remain relevant 20 years later.

(5) Ice Cube over (12) Scarface

In a battle between two emcee’s who are known for vivid raps about the systemic struggles of inner-city Americans, Cube’s broader appeal gives him the edge over Scarface in a tight one.

(11) Redman over (6) KRS-One

The Funk Doctor pulls off the upset, beating out KRS in a close one and proving that Knowledge Reigns Supreme Over Nearly Everybody, but not Redman.

(8) Kanye West over (9) 50 Cent

In 2004, 50 would’ve wrapped up this match early, but though 50’s record sales and ’01-’04 run are undeniable, it’s been all Kanye since.  Mr. West wins convincingly.


Region D

(1) Tupac over (16) Eve

The First Lady of Ruff Ryders is no match for the icon that is Tupac Shakur and his Thug Life teachings.

(2) Outkast over (15) Dead Prez

ATL’s finest crush Dead Prez in another rout as the power of Aquemini is too much for the revolutionary emcees to withstand.

(3) NWA over (14) 8Ball & MJG

The group who popularized gangsta rap on their way to commercial success not only scared America in the early 90’s, but they also defeat the influential Tennessee duo handily.

(4) Lil’ Wayne over (13) Queen Latifah

The Young Money Millionaire’s 10+ year run of steady ascension to the forefront of hip-hop’s current-day elite beats out Latifah’s impactful but short-lived reign as hip-hop’s Queen.

(5) Public Enemy over (12) Da Brat

PE Fights the Power and also fights their way to a close victory over the first female solo emcee to go platinum, proving once again that it takes a Nation of Millions to Hold Them Back

(7) Nicki Minaj over (10) EPMD

The funk-heavy tunes of EPMD in the 80’s and early 90’s pioneered a sound that was influential, but fail to edge out Nicki’s creative delivery and lyrical prowess.  The Green-Eyed Bandit is no match for this talented and rising female Monster.

(8) Rick Ross over (9) Mobb Deep

The Infamous Mobb falls short against the founder of Maybach Music proving that Ricky Rozey is no ‘Shook One’.

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