Words By: Keith Nelson Jr (@Jusaire)
It’s 9:20 A.M. on October 30th, 2015 and Oswin Benjamin is sitting in the SiriusXM studios having his confidence tested by legendary hip-hop journalist and Sway in the Morning host Sway Calloway. “A lot of n*ggas up here think that they nice and they come up here and they crash,” Oswin remembers Sway telling him. “Yeah, a lot of n*ggas be wack,” Sway in the Morning co-host Heather B chimed in as Oswin sat by himself in the lobby couch. Sway would later tell the 22-year-old MC he only does that to make nervous MC’s more nervous.
He wasn’t nervous. He was hardly even listening. Drowning out Sway’s words were thoughts of the show in Kansas he and his manager Tyler Busher were on the verge of planning accommodations for. They had just been informed the previous day that Oswin had been removed from the bill three weeks prior with no notice. Those thoughts ping-ponged off thoughts of his long time best friend Spencer who called out of work and was preparing to drive 20 hours to that same show in Kansas.
Fast forward a few weeks to November 19th, 2015. It’s 9pm in the basement area of a dilapidated project building in the Bronx, NY where me I go to meet with Oswin and members of his close-knit team. I’m greeted by exposed sheetrock, hanging light wires and the remnants of an apartment still under construction. Oswin’s perpetual smile can be seen through the forest of dreaded hair and is only momentarily replaced by a concentrated gaze whenever he begins reliving a moment close to his heart.
It is in these subtle nuances and comfortability in the most precarious living situations that I quickly realize something glaringly true: young Oswin’s roots runs deeper than a freestyle.
Chapter I. All Church In The Wild
“I was in the shower one day, and I was singing and my brother was like ‘what is that?’ I was like ‘I don’t know. I don’t know where it came from.”
In the mid-90s, one of the future great up-and-coming MC’s was more Kirk Franklin than Biggie. Over a decade before he ever heard Jay Z’s debut album Reasonable Doubt or had any interest in rapping, a five-year-old Oswin was a gospel singer part of a group called Voice of Joy. Along with his brother Joel and a few of his god brothers, they performed in at churches in his birthplace of Brooklyn, New York costumed in “turtlenecks with the logo on it.” If it wasn’t for the group breaking up, Oswin’s first introduction to the world would have been on a Patti Labelle album, according to him.
The visceral images Oswin paints with vivid detail on songs such as “The Soul Pt. 2” are the hallmark of an MC who would rather connect with you emotionally than wow you lyrically. He recalls moments in his life from over 10 years ago, like his time singing in church, with yesterday clarity; a sponge who will turn anything his friends say around him into a witty comeback within seconds. That steel trap of a mind has also imprisoned Oswin’s conscience at points in his life.
One day while he was in elementary school in Brooklyn, a classmate told Oswin his mother had performed oral sex on him the night before. “When he said that, I’m eight years old, and I’m seeing my moms sucking this nigga’s dick,” Oswin remarks with his eyes bulging as if trying to escape the memory, physically. The next day, with the images now woven into his subconscious like blood in a carpet, Oswin approached the kid and, well, roll film: “It was like a movie. ‘Yo, son, what you said about my mom yesterday, son? He was like ‘yeah your mom was sucking my dick.’ So I took the safety pin out the envelope and I stabbed him in his eye,” Benjamin retells with an unblinking gaze.
Karma and some unexplained incidents took away Oswin’s vision in his left eye by the time his family moved to Newburg, NY at the age of eight. The MC who turns observations into gold became self-conscious when his lost eyesight caused him to be ridiculed by peers, forced to wear Horace Grant-style goggles during an era when everyone wanted to be like Mike. He feared fully applying himself because the outside world, including his own reflection, told him he was limited, a fear that still persists. “That fear translated into a lot of shit as far as anything I did [that] I never did 100 percent. It was all off of that one experience.”
Chapter II. Jay Z Taught Me To Be Human
Back in 2008 Oswin was in the cafeteria at Nyack College encircled by a ravenous crowd of meal plan- depleted college students currently being fed Oswin’s dark carcass by someone peppering him with jokes. “It was a scene from a movie,” Oswin begins, leaning into the recorder resting on the table with a stoic glare. “Niggas were battling in the cafeteria and this one dude started cutting my ass about how Black I was. I was wearing fake Prada’s. Everything I had was 100% fake.”
With his soon-to-be manager Tyler Busher watching, unbeknownst to the MC who was becoming increasingly enraged with every joke, Oswin heard “‘Yo Os, you gon let a n*gga cut ya ass like that.’” Oswin smirks at the recollection before revealing what he did in response. “Just like a movie, someone started beating the table and I started rapping, freestyling,” Oswin says passionately, swaying his arms as if trying to recreate the scene. “I don’t know what happened but I must have been cutting his ass for a minute and a half, two minutes, straight.”
That was the first time him and his manager ever spoke. “He didn’t fuck with me before because he was like ‘this n*gga wearing fake shit.’ But then he came up to me like ‘yo, my n*gga, you really rap?’”
Growing up in a house of gospel, Hip Hop was damn near outlawed. “It was really strict on the type of music we would listen to,” Oswin says. “So I didn’t start listening to music outside of that until I got to college.” In a sense, Hip-Hop was the Adult section in the video store shielded from view by rows of beds anyone can easily enter. Oswin was not necessarily a cultural tourist, but it was a forbidden island he had a loose ancestral connection to.
Before you can discern the contextual clues, historical references and even the colloquialisms from a culture you’re new to, people tend to gravitate towards what represents an obvious extreme. There were tons of kids who got into basketball at the turn of the century that would debate you until their Danimal packets burst through the slits of their fingers about Vince “he put his arm in the fucken rim” Carter being a better player than Kobe Bryant. Not because these new basketball fans appreciated how Vince Carter spaced the floor with high basketball intelligence. But because Vince Carter put his fucken arm in the rim, and no one did that before, so therefore Vince Carter is one of a kind and the best player in the world. Hip-Hop operates under a similar logic, sometimes.
“I felt the reason I liked Nas was because I couldn’t understand him,” Oswin explains about his early days as a Hip-Hop head. Oswin was new to Hip-Hop so he broke it down a very scientific way, even employing dubious methods, inspired by Nas, to gain acceptance. “Before, when I would rap, it would just to prove to n*ggas I’m nice. If I throw a bar in there about the stars and the universe or whatever, n*ggas is going to automatically think I’m nice.”
Jay Z changed that. When asked if Jay Z made him human, Oswin wastes probably half an eyeblink before responding with a convincing “yes.” “It’s because, n*ggas would say shit like ‘Jay Z just be stunting.’ But, that n*gga just told his reality.”
In his relatively short career Oswin has faced rejection most aspiring rappers dream to get. In late 2012, Kendrick Lamar was interviewed by AllHipHop.com’s co-founder Chuck Creekmur for Apple’s “Meet The Musician” event in New York City. When Creekmur opened it up for audience questions, Oswin was in attendance and asked if he could spit a 16 for the good kid, mAAd city lyricist. Creekmur attempted to disallow it before Kendrick let the young MC spit a verse. Unfortunately, Oswin’s audition for the TDE titan was cut out of the official podcast of the event and only exists as a deleted scene in his mind.
Two years later, Kendrick’s labelmate Ab-Soul was being interviewed by RapRadar’s Elliott Wilson for the “CRWN” series in New York City. Oswin again asked to spit a verse, but this time, the moderator was a bit more aggressive in his refusal. “Elliott Wilson was like ‘oh, come on, nigga we not doing that here. Nah, this is my show. Niggas don’t rap on CRWN.’” But, once again, the rhymes prevailed. Ab allowed Oswin to spit and even congratulated the young MC.
These experiences and a tenacious spirit have brought him through the fire, but not unscathed. At the time of this interview he is living unemployment check to unemployment check (a safety net that collapses months later). Eviction is a forgone conclusion and he is tempted to take the route of fast illegal money.
But, as he stood in the SiriusXM studios in front of a microphone next to proven battle rappers K-Shine and DNA, he maintained humble yet unwavering eye contact with Sway as he began the show’s weekly Friday Fire Cypher. There were no doubts in his mind. Only bars.
“When they were rapping, I wasn’t even listening. I was putting verses together. I started getting nervous ‘cause way more verses started coming to my head.” He remembers that transformative moment in his career as vivid as any other scene in the self-directed film he calls his life. He even broke down a few bars from the session:
“unemployment got me thinking about narcotic sales.”
“I thought that was the perfect segway because I told Sway about being unemployed.” The allure of being told all he would have to do is meet with someone and transport a bag to get $1,000. “N*ggas was offering all types of shit. ‘Yo Os, make this trip, you gon meet this n*gga. Every trip you make is $1,000.”
“God it’s getting hard, so can you lend a hand to me/it’s starting to feel like the Devil is lending his hand to me, and this curse looks like a blessing that he’s handing to me.”
“Do I take this and make this bread? God is this what you telling me to do? Is this my way out? This was real shit that was going on then that is still going on now.”
Oswin released a mixtape, Soon You’ll Understand Vol. 1 on January 10th, featuring him eviscerating classic Dipset and Roc-A-Fella production. While the project is sure to satiate his growing fan base thirsty for punchlines, it’s his upcoming project Protect Your Soul that left me paralyzed in my seat when he previewed a few tracks for me on that November night. Entirely produced by beat wizard Beewirks, Protect Your Soul sounds like an MC unbinding his talents to preserve his legacy. Songs like the “Lights” features Oswin returning to his singing roots and the soul-infused “Home” has Oswin “analyzing my last breath.”
Oswin Benjamin wants to give it his all, because he knows that’s the only way he knows how. “If all you get from me is that n*gga can rap, I didn’t do my job. That’s not what music is about.”