Virginia native Masego has spent the past several years dismantling music criticism’s beloved “high art versus low art” argument through his unique brand of “trap house jazz.” In his world, the two genres, both deeply rooted in Southern black culture, get along with each other fairly well.
“I can do that because when I show a person who is just in that trap world a musician, it’s just blowing their mind,” says the multi-instrumentalist, producer, singer and rapper, who also sometimes goes by the alias Uncle Sego. “It doesn’t have to be the first-chair, all-city musician, but he’s just coming with some fresh ideas. Then you bring a trap person who isn’t a musician and you hear the cadences they do when they rap — we can help each other.”
Masego has found an interesting way to combine his appreciation for jazz greats like Cab Calloway (whose “Hi-De-Ho” chant has become one of his signatures) with his love for 2 Chainz and O.T. Genasis, all while being mentored by the likes of hip-hop legend Jazzy Jeff.
“It changed my mentality,” says Masego of working with the DJ/producer best known as Will Smith's partner in hip-hop. “I didn’t want to collaborate as much until I started being around him. It helped chisel my craft. My songwriting got better because Jeff cares about lyrics. He opened up his home for me to stay there for like a month while I created whatever I wanted.”
That environment allowed Masego to finish his breakout project, Loose Thoughts, on his birthday (which he shares with Kanye West) and release it last year alongside Pink Polo, an EP collaboration with Soulection-affiliated producer Medasin. He even hooked up with Grammy Award–winning duo Brasstracks (Chance the Rapper’s “No Problems”) to do vocals for their track “Melanin Man.”
Just two years prior to all that, Masego — born Micah Davis to Jamaican parents — couldn’t find a crew, fan base or place. “I didn’t even have fans when I was coming up with this,” he explains. “I was like, ain’t nothing can hurt me now. They weren’t fully on me in the jazz community and they weren’t pulling me into trap. I was like, I’ll try my own thing.”
It didn’t help that Virginia, where he grew up, isn’t considered a huge music hub, despite being home to regional notables Wale and GoldLink — both of whom Masego has worked with. Regardless, that type of isolation often fosters creativity out of necessity.
“Virginia is a place that’s so boring, you find friends and do cool things,” Masego says. “I swear we did nothing but have jam sessions at my house and listen to a bunch of different music on YouTube. It became a musical gumbo. Whatever we were into at the time, we just tossed in the pot. People were like, 'I don’t know what this is, but I like it.'”
Masego spent a large portion of 2017 touring the world with his Trap House Jazz Band, getting endorsements along the way from the likes of 1800 Tequila and JBL audio (for Quincy Jones’ special line of headphones). He didn't release much new music outside guest features on tracks for Jazzy Jeff, Chon and Top Dawg Entertainment’s newest signee, SiR. But Masego's time is now and he totally understands that.
“I looked how much my rent cost and I found how much Spotify paid me — I was like, I’m good,” he says. “The moment you’re not worried about adult problems and you get to just make music, then I’ve made it to some extent.”
The biggest trick up his sleeve for the year is “Navajo,” which is already looking to make a few “best of” lists by the year’s end. The buttery smooth joint continues his run of bringing new collaborators into his world.
“I finished [it] at Jazzy Jeff’s house and Muhsinah is this super-talented singer-songwriter who helped me decode my mumbles,” he says. “She was listening to it and was giving in all this great input, like a musical therapist. I play it for Jeff and he’s like, 'We gotta get the drums to knock more.' He made the drums knock and it was crazy.”
“I think it’s a matter of me getting some quiet time to really say: What cohesive story do I want to tell?” he says of his next moves.
As hip-hop sits on the top of pop music’s food chain, Masego represents a new class of artists stretching the limits of the culture by embracing damn near everything. Hell, the closer of Loose Thoughts is actually titled “I Do Everything!” and has him bragging about the dozens of musical instruments he can play, on a track on which he both sings and raps in triplets (or as the young kids say, “Migos flow”).
“You see the climate,” Masego says. “You’re allowed to be a little bit weird and still get massive attention. The fact that a Solange can work or a Daniel Caesar can work or even how far Kendrick Lamar has gotten. People are getting more comfortable.”