(1) Notorious B.I.G. defeats (9) DMX
DMX’s bark proves to be louder than his bite against Biggie. The Brooklyn emcee unleashes a lyrical fury that his Yonkers counterpart cannot withstand, and then proceeds to party and bullshit and party and bullshit!
(2) Snoop Dogg defeats (7) Eric B & Rakim
In the ultimate show of respect for his old school counterparts, Snoop Dogg remade Eric B and Rakim’s classic track, ‘Paid In Full’ on his 2001 album ‘Paid The Cost To Be The Boss, with his version entitled Paper’d Up. And while this made it difficult to give Snoop the edge over Eric B & Rakim, he wins because he simply has more hits and a longer run of relevance to his credit.
Rakim was a groundbreaking lyricist and along with Eric B, their run from 1987’s ‘Paid In Full’ through 1992’s ‘Don’t Sweat The Technique’ (which included the title track for the feature film ‘Juice’ starring Tupac Shakur) was brilliant. Snoop’s run however spans from his 1992 unforgettable appearance on Dr. Dre’s ‘Deep Cover’ to current, a run that includes 17 Grammy nominations. Even Rakim’s successful 1997 solo release, ‘The 18th Letter’ isn’t enough to upend the D.O. Double G as Snoop wins going away, lights up what we’ll just call a victory cigar, and advances to round 3.
(3) Beastie Boys defeat (6) Salt & Pepa
In the battle of two iconic rap groups, and what proved to be the closest round two match-up in this region, hip-hop’s first ladies fell just shy of upsetting the boys from Brooklyn. While Salt & Peps paved many lanes for not only females in hip-hop but also rap groups in general, the Beastie Boys also smashed doors open by expanding hip-hop’s color lines and proving that a Rap group could grow artistically and reinvent itself without renouncing their hip-hop roots. Push It they did, but Salt, Pepa, and Spinderella had no answers for the Beastie Sabotage.
(1) Eminem over (8) Lauryn Hill
Eminem faces a far greater female challenge in the Round of 32 as he squares off against L.Boogie. Both are highly talented lyricists, but one is greater than the other. Both are highly decorated; Hill has 8 Grammy’s and 19 nominations. But Mr. Mathers has 13 wins and 39 (!) nominations. It’s gonna take some serious muscle (or a chainsaw) to take down Slim Shady.
(6) Ludacris upsets (3) Missy Elliot
In an upset, Ludacris takes down Missy Elliot on the strength of 7 straight years with at least one Grammy nomination from 2002-2009 (taking home 3 in that span) and following that up with at least one nomination every other year thenceforth (’09, ’11, & ’13). His consistency as a force in the game since he broke through with Word of Mouf in 2002, along with his mastery of the couplet gives him the edge over Missy who peaked from ’95 –‘06’ (winning 5 Grammys along the way) and has been a presence, but not a dominant one in hip-hop since.
(7) Talib Kweli over (15) Mos Def
Due to an upset in the Round of 64, we end up with an inter-Black Star squabble. While their greatest work is as a duo and while Mos’ Black on Both Sides is a hip-hop classic, Talib’s higher profile between 2002-2004, featuring smash hits with Kanye West, along with a flow unreplicated in hip-hop, give him slight edge and ultimately the victory.
(1) Jay-Z over (4) Kanye West
Despite his 21 Grammys, Kanye falls short against Brooklyn’s Finest (not far behind with 17 Grammys to his name) in a classic example of the teacher still having too much in the tank for the student to overcome.
(3) Nas over (11) Redman
In a match-up of veteran lyricists, the Queens Bridge emcee’s critical acclaim and commercial success give him the edge in a close one over Brick City’s finest. Tough loss for Redman as Nas advances to the sweet 16.
(4) LL Cool J defeats (5) Ice Cube
In a tight one, the battle of two emcees with similar career paths comes down to the wire. Both men helped elevate the game in the late 80’s and early 90’s, LL as one of rap’s early cross-over stars, Ice Cube as the lead voice of rap’s Most Dangerous Group, NWA. Both went on to success on screen, landing roles on network tv shows, movies, and in Ice Cube’s case even putting out his own line of movies with Friday and Barbershop. Both are still recording today. In the end, LL’s broader musical palette, creating both hard core hits and becoming a master of the Rap ballads when combined with his 2-0 Grammy advantage is just enough for LL to win the match. Mr. Smith survives and advances, but with NWA a heavy player in Region D Ice Cube may get a shot at redemption. Stay tuned.
(1) ‘Pac over (8) Rick Ross
To use Rick Ross’ words, “Tupac’s back!” And back with a vengeance at that, as the West Coast rider (who was born in Bronx, NY) has no problem defeating Ross, in hologram form no less.
(2) Outkast over (10) Nicki Minaj
The duo from ATL win, looking Nicki Minaj in the eye and proclaiming that “roses really smell like pooooooooo oooo ooooo.”
(3) NWA over (6) MC Lyte
The boys from Compton simply have too much firepower (pun intended) as the combined talents of Dr. Dre, Ice Cube, MC Ren, and Eazy-E are too much for MC Lyte to withstand. She wanted a Ruff-Neck, she got several.