Comedian-actor DeRay Davis might be full of jokes, but he’s not playing with Hip-Hop.

His connection to Hip-Hop goes beyond skits and punchlines. The Chicago-born entertainer has teamed up with Harlem street veteran Nino Man for a new single that blends their unified charisma with gritty New York-type bars.

For longtime Hip-Hop heads, DeRay’s presence on a track isn’t as surprising as it might seem.

He has been orbiting the culture for decades, from classic skit appearances on early albums by Kanye West to cameos in music videos. But, this pairing with Nino Man, who is a respected Harlem lyricist, adds a different level of authenticity to his CV.

On the track, Nino Man delivers his trademark Harlem slick talk while DeRay leans into clever wordplay. It’s not novelty rap. It feels more like a late-night cypher. People may not admit it, but this chemistry reflects how comedy and Hip-Hop have always overlapped. We have not forgotten those Def Comedy Jam stages or movies like Friday.

For Nino Man, the collaboration helps his reach beyond the streets of New York. For DeRay, it’s proof that his Hip-Hop roots are still alive and he can actually rap. Fans who remember his early Kanye skits or his hosting run on Hip Hop Squares know he’s always been embedded in the culture. But this is a new level for him.

Hip-Hop is paying attention.