We have reached the second round in the ultimate battle for the title of the GOAT (Greatest of All-Time). We are asking you to help us rank who is the greatest MC to pick up a mic. We will take over 35 years of Hip-Hop into consideration, pairing special match-ups in a “playoffs style.” Since Fall 2014, and for the next several months, we will roll out battles, starting with artists from similar eras paired against one another, until one undisputed King or Queen of the microphone reigns supreme.

Two artists who came to form in opposing sides of New York City at the same time, Kool Keith and Big Daddy Kane have both been leading innovators, ceaseless performers, and artists who transcended simply being MCs since their simultaneous mid-’80s beginnings. One artist has two gold albums, a friendship with Madonna, and became an icon of Black culture. The other artist has released, between solo and group, nearly 30 albums. These works, nearly all independent, influenced Hip-Hop, Drum & Bass, and Trip-Hop hits and movements, with various visual components. Brothers in arms, Keith and Kane each have done it their way, on their specific terms, and they are all definitely still doing it. Regularly touted as Greatest Of All Times by their fans, watch these two living legends square off to advance to Round 3 (click on one to vote).

Voting For Round 2 is now closed. Stay up to date with the latest Finding The GOAT brackets

Big Daddy Kane (First Round Bye)

In terms of commanding mic controlling, Big Daddy Kane staked his claim early. The Brooklyn, New Yorker emerged in the mid-1980s battle-scene carrying a unique balance of lethal confidence and unaffected smoothness. Antonio Hardy is able to rap extremely fast, making a nonstop case for his supremacy as an MC. After linking with Marley Marl’s Juice Crew, King Asiatic began work on 1988’s Long Live The Kane, one of the highest-regarded Hip-Hop albums of all-time. Big Daddy was a master at blending audiences, by offering something for lyric-seekers, routine lovers, ’70s R&B fans, as well as those simply thriving upon vibe. Arguably more so than other elite GOATs, Big Daddy Kane took a gold-certified style, and adapted and tooled with it on each LP, from the seductive (Taste Of Chocolate) to the hardcore B-boy (Looks Like A Job For…). Never a Top 10-selling artist, Big Daddy Kane is a stone in the sand reminder that skills may be the tortoise to the hare, and artists can reach sales benchmarks simply based upon quality.

Following 1998’s Veteranz’ Day, Big Daddy Kane has shunned solo albums for more than 15 years—leading some to question his ability to command an album in the new millennium. However, as evidenced in the Dave Chappelle’s Block Party music documentary, Kane’s live show—which he offers regularly—dwarfs his Rap peers, 20 years his junior. The confidence, moves and finesse remain in tact. In critical guest spots ranging from Big L to Little Brother, Kane teases Heads with deft lyrics that are to the level he produced in the ’80s and ’90s. Like a champ with the belt, Big Daddy Kane walks uncontested—a GOAT in his own, and the minds of legions of others. In history, weighted upon influence, album-making, and pinnacle star-power, Big Daddy Kane just might be the original, and perhaps the only GOAT.

Other Notable Songs:

“The Symphony” (with Kool G. Rap, Craig G and Masta Ace) (1988)

“Warm it Up Kane” (1989)

“Young, Gifted And Black” (1989)

Kool Keith (First Round Wildcard Winner)

Although he may be remembered as simply “kooky” in the history books, Kool Keith is first and foremost one of Hip-Hop’s most innovative, and uncompromising lyricists. Starting with Ultramagnetic MC’s Critical Beatdown, Keith took the mid-’80s style of rapping and began playing with delivery, flow, and overhauling the vocabulary masters of ceremony used. Keith was the equivalent of the introduction of the electric guitar to Rock music, in terms of what he brought to the tradition of MC’ing, and the Bronx, New Yorker opted to be different at every bend in the road. In a series of albums since the Ultra Mag days, Keith has continuously worked to advance the craft, and challenge the status-quo of Hip-Hop.

To consider Keith Thornton a GOAT is to place value on imagination and creativity. Especially since year 2000, Keith has countered the expectations of even his most devoted fans with incarnations, albums, and styles that range from odd-ball to highly pioneering, if not off the radar. At a breakneck pace of releases, the bi-coastal wonder remains active in touring, with shows as distinct as his microphone manipulations. From the aforementioned Beatdown, to Four Horsemen, to Dr. Octagonecologyst, this MC has fan favorites and widely-heralded albums by fans of rapping, production, and advanced Hip-Hop style. Kool Keith cannot be pinpointed, and after 30 years on wax, he’s still housin’ things with originality, sass, and disdain for MC convention.

Other Notable Songs:

“Poppa Large” (with Ultramagnetic MC’s) (1992)
“You’re Late” (with Cenubites) (1993)
“20 Chevrolets” (2001)

So…who you got?

Related: Check Out The Round 1 Ballots & Results