Playtime Is OVER. Oswin Benjamin Has The Best Freestyle Of 2019

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Oswin Benjamin has been on the grind in Hip-Hop for years. The New York City lyricist has made his appearances count, whether they were high-profile freestyles, Team Backpack cyphers, or features on Styles P, Anoyd, and Domingo albums. The close affiliate of Chris Rivers has just released his full-length debut, Godfrey. After waiting patiently, he deserves all of the attention.

In raising awareness for the independent LP, Oswin stopped by Sway In The Morning for a jaw-dropping clinic that takes 2019’s freestyles to a new plateau. Benjamin left bruises on the microphone as he bodies nine different beats over 10 minutes. This Big Apple-based MC waves off the notion of “5 Fingers Of Death” with a two-fisted display of dope MC’ing. This freestyle has incredible substance, style, and stamina—all at once.

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Beginning with JAY-Z’s “Ignorant Sh*t” instrumental, O raps about his journey to get to Sway’s spotlight, a gesture that he does not take lightly. Each time DJ Wonder changes the beat, Benjamin’s flow grows more animated and impassioned. His words bring Superman to the Bronx, with a series of references to the superhero and characters within that universe. The sprawling bars use God a motif as Oswin returns to the bumpy industry road that he has witnessed. Throughout, his similes pull from interesting places in pop culture, from Empire to D-Block to the Dungeon Family. “I’m constructing these euphemisms for you to listen / I use the truth to expose the gimmicks / Imploded feelings revealing the sinning Christian / Double-crossing God like two Nazarenes at the Crucifixion / Before the locks couldn’t get the P or a kiss for nothin’ / When I would kill-a-mic at every show and see low green / And big boy would dream to get his family out the dungeon / Make ni**as look up to the bars on some bottom-bunk sh*t,” is one such dazzling excerpt.

As DJ Wonder drops the needle on Pete Rock’s “They Reminisce Over You” instrumental, Oswin hits an even tighter pocket with his flow. His references elevate too, from 1980s cinema to 1990s Nickelodeon morning cartoons to Quality Control superstars. “Look, I ain’t political / I’m just a god with a sinner’s view / Ridiculed for how the spirit moved / You ever seen a survivor of a Robin Williams-type of depression? Well this dead poet is livin’ proof / I did my dirt on the come-up though / I dug trio, left, skeeted mayonnaise on some patties, a Doug trio / Offset by their ways, when they take off, broad for amigos / That’s when I Takeoff like a Migos.

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By the time Wonder reaches Nas’ “One Mic” beat, Oswin is in sixth gear with his foot off the clutch. The passionate delivery urgently pushes out clever bars of wisdom. He condemns institutional racism, from what is in the textbooks to what history shows. The incredible rap compares the hammers used to enslave Black people with chains to the judge’s gavel in a system where justice is not always reflected in verdicts or sentencing. This incredible section follows a beat transition into Kendrick Lamar’s “Sing For Me, I’m Dying Of Thirst.”

In the final minute, Oswin’s imagery moves to baseball, covering everything from the bases to the bullpen to tobacco-spitting players. He switches to art, referencing the late Keith Haring and painted murals. Notably, he nods to the 2017 freestyle that made him go this hard. “Black Thought blacked out and inspired me / Condolences if you’re following behind me / R-I-P to Nispey and those casualties,” before adding “I know it may sound cheesy, but rest easy, Mac / They don’t pray for us, they prey on us / They scream ‘rest in power’ to give power to vices that dig the grave for us / All those memorials and murals is cool / Y’all ni**as sleep, but when you gonna find the gumption to wake for us / Don’t wait, until the wake, to pray for us / Don’t wait until Jesus walks to ‘yay!’ for us / Clap for me and encore before I’m part of the funeral parlor decor / Let me smell the rose / And let your praise be the praise I redirect to the Messiah before he take me home, ni**a!” Oswin Benjamin ends with a crescendo after delivering a freestyle that will be mighty hard to top.

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#BonusBeat: Oswin Benjamin’s “Yessuh” music video from Godfrey: