As we continue 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 sequence not unlike March Madness. 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.

The next two MCs to square-off arguably are the two biggest developments in Hip-Hop between the deaths of 2Pac and The Notorious B.I.G. and the arrival of Kanye West: 50 Cent and DMX. Each artist enjoyed some of the strongest sales runs and industry dominations ever had. Taking what they learned from the 1990s and bringing it to a digitized culture in the 2000s, it’s hard to imagine Rap without either of these New Yorkers. Read these quite different backgrounds and histories, and cast your vote.

50 Cent

As Hip-Hop started to live online, 50 Cent grabbed it and brought it back to the streets of Southside Jamaica Queens. A onetime protege of Run-DMC’s Jam Master Jay, the brolic lyricist would not break, would not budge, and would not back down from anything. Shot an astounding nine times to prove it, Fif gained notoriety in the late ’90s for fearlessly challenging/poking fun at the industry at a time when commercial Rap music was still smoothing itself out in a post-Death Row vs. Bad Boy world. Unafraid of anything, 50 Cent was Rap’s ultimate bull in a china-shop. 50 Cent made headlines, he made hits, and he left marks along the way.

Signing with Eminem after a botched Columbia Records deal with Trackmasters, Curtis Jackson used the weapons around him (Dr. Dre and Sha Money XL’s ears, Interscope’s combative marketing, DJ Whoo Kid) to roll out like no other artist before him. Fif used mixtapes and free product to bring the streets to a boil before releasing Get Rich Or Die Tryin’ to instant, skyrocketing sales and acclaim. Along the way, 50 used his records as declarations of war, starting with Ja Rule, and continuing with nemeses such as Nas, Diddy, Fat Joe, DJ Khaled, Jadakiss, Rick Ross, and even former band-mates Game and Young Buck. The ultimate Rap war-monger, 50 Cent took the studio wrestling parallels of mainstream Rap, and became Vince McMahon. But for every Robert De Niro and Al Pacino co-starring film, for every Chelsea Handler romance report, and every Vitamin Water report in Forbes, 50 was still posted up in the streets, delivering confrontation, street rap, and the mixtapes that turned a hustler into a mega-millionaire.

While Hip-Hop left the 1990s mourning several of its icons, 50 Cent re-captured that pre-1996 energy. It was 50 Cent who made album cuts into de-facto singles. Fif made award shows interesting, built an empirical label, had moments of hubris, and is still living to tell them—in a completely new chapter. The head of G-Unit Records remains a tour de force on and off the microphone, and proof that it’s not always how you say it, but what you say. Although his flow, lyricism, and metaphors have not been in Rap’s most elite class of the 2000s, 50 Cent continues to rap with a conviction, sincerity, and lived experience that is hard to rival throughout the ages.

Other Notable Tracks:

“Fuck You” (2002)
“Back Down” (2003)
“Rider, Pt. 2” (with G-Unit) (2008)

DMX

In the days following the tragic murders of 2Pac and The Notorious B.I.G., while Nas, Jay Z, AZ, and others vied for the crown of East Coast Hip-Hop, no relative newcomer made a harder, faster, and more ferocious fight for the throne than DMX. Not a newcomer at all, the Yonkers, New Yorker had spent the decade rhyming, a previous beneficiary of major label deals, and known on the battle circuit by everybody from Jay to Percee P, care of the Stretch & Bobbito show. That competitive energy fueled a fire inside of X, who treated every track like a battle, even if with himself.

Similar to the image of ‘Pac, DMX’s words and presentation married the grittiest of the streets with sensitivity, vulnerability, and full dimension. A Ruff Ryder, DMX had the swarm of the Wu-Tang Clan with the menace of M.O.P’s First Family. In his late 1990s Def Jam run, X presented the perfect backdrop to his explosive delivery: subtle references back to the Hip-Hop of NYC’s glory (EPMD, LL Cool J, Chuck D), with booming new sounds, courtesy of Swizz Beatz, Dame Grease, and others within the R.R. posse. DMX was the perfect vessel to suggest a rawness “up top” on the Rap map, while his backdrop played into “down bottom.”

Moreover, X’s message inspired others. Although the artist’s legal issues, and unmovable chip on his shoulder towards labels, peers, and the industry were stationary, DMX worked with nearly everybody, bridging a factioned, territorial climate in the genre. Clearly walking as the alpha-dog, Earl Simmons commanded his message, and helped accelerate the labels and industry to the pace of the would-be Internet culture. It was DMX who, alive, could release two #1 albums in the same year. It was DMX who could follow singles deemed too raw for radio and video with crossover tracks. With X in the lead, he opened the doors for not only friend-turned-foe Ja Rule, but also helped ONYX gain renaissance, and create diversified lanes for his crew-mates The LOX, Eve, Drag-On, and Swizz. Few artists in “the shiny suit era” (which arguably X’s success marked the end of) had the perceived authenticity, unpredictability, and tangibility as DMX.

Other Notable Tracks:

“Murdergram” (with Jay Z & Ja Rule) (1998)
“Slippin'” (1999)
“Put ‘Em Up” (2010)

So…who you got?

Voting For Round 1 is now closed. Stay up to date with the latest Finding The GOAT brackets

Related: Check Out The Other Ambrosia For Heads “Finding The Goat” Ballots