Masego’s many layers
Lady Lady proves the creator of “trap house jazz” doesn’t have to be one thing.
Masego’s many layers Courtesy Masego

Before we got on the phone, one of Masego's relatives chucked a water bottle at his head. He hadn’t had enough H2O that day, and, well, the women in his family don’t play. “I have a knot on my head,” he says over the phone from southern Virginia, where he’s spending time with family before his worldwide tour. “But I also drank water today.” The Newport News native was raised by independent women, and his debut album, Lady Lady, is partially the result of lessons learned from them over the years. “Women who care about your health is such a cool thing,” he says with a laugh. “Your homies won’t remind you to not eat gluten.”

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Lady Lady, out now, presents Masego as the musical polymath who’s equally funny, flirtatious, and sensitive. He’s the young man with an uncle’s persona, the slick-talking gentleman who can two-step at the cookout and turn up at the festival. Across 13 tracks, the 25-year-old recalls the despair of heartbreak and forecasts the joy of singing to his bride on the altar. He’s also the playboy, using his fame to play the field. As a musician, Masego pulls from many different genres, all of which inform his midtempo blend of self-described “trap house jazz,” where R&B, smooth jazz, and staggered rap flows are funneled into a seamless electronic bounce.

Lady Lady is the culmination of Masego’s past five years of dropping remixes on his Bandcamp and Soundcloud pages. In 2016, his work caught the attention of veteran producer DJ Jazzy Jeff, and he now counts vocalist SiR and TDE producer Sounwave as collaborators, on “Old Age” and the title track, respectively. Lady Lady is a multifaceted take on romance, heartbreak and love; it’s another step in the young artist’s trajectory, proving that he doesn’t have to be one thing. Love ballads, pop songs, soul music, he’s got you.

How did you take all of these sounds and blend it into one thing?

The house I grew up in, my room has 200 pieces of vinyl on the wall. So Stevie’s to my left, preQuincy to my right, Cab Calloway’s in front of me. Aretha’s over here. It’s literally all these different people. Then also, most of my friends are from the hood, so they’re always giving me the actual drug-cooking music with the hard-hitting drums. I guess it’s the cloth I’m cut from. I really like a bunch of different things and I like to find different ways to make everybody appreciate the same things I like.

Your music also has a distinct international feel to it.

I wish I was that calculated with the moves, but it’s just kinda how I am because I have so many friends from overseas. In Virginia, there were always military people in town, so every week I’d meet someone from a place I’d never been to. They’d give me some of their culture and slang and what not. Then once I started traveling overseas, I naturally gleaned some of that culture and art, and fell in love with so many elements. I think of it like battle rap: you take in whatever’s bothering you, then when you have to recall it in real time, whatever you ate is coming out in that freestyle rap. So everything that I make is literally the most recent thing I’ve been eating.

So what were you consuming during the creation of Lady Lady?

It was a reflective time of my life. After I had a full year in L.A., I got to think about where I’d come from. I remembered that there was a woman at every checkpoint in my life who brought me to where I’m at. I started thinking about my exes, like ‘When I had a confrontation with this woman, that was also impactful.’ Then there was another time when I talked to my friend about his relationship and that impacted me. I reflected on all of that with the creation of Lady Lady. It was very therapeutic as well; with some relationships, I didn’t understand why it devolved. With some others, I wanted to be in a place where I could continue this relationship, but I couldn’t. I thought about where I will be in 5 or 10 years: Will I be in the mind state where I’ll be wedding-ready? Some of these songs reflect a deeper corner of love that I haven’t even experienced yet. It was a very cool mental exercise.

“Black Love” really stuck out. It feels like a wedding song.

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I was even surprised I could write that, because I am not that deep in love right now. That’s how I knew it was literally a gift for me to tap into that genuine feeling and translate it to a song. I was on a train ride to go see this girl for the first time. I’m obsessed with her already, just off of some pictures, on some young boy tip. I’m on the train this entire time, playing out different scenarios in my head, and I’m listening to Chantae Cann’s “Find My Way To Love.” That song is the most cloud-filled, beautiful flowers-y song ever, so I fall asleep listening to that. I pretty much write the song while I’m sleeping and then wake up singing the melody. “Black Love” made my mama cry, so this is one of those song songs. When I hear it, it makes my heart do some things.

Masego’s many layers
“I pursued my own lane based on how much wasn’t around me.”

How has your upbringing in Newport News influenced the music you make now?

Newport News and Virginia in general made me curious about what else is out there. I heard a lot of neo-soul in the city, and because of the way Virginia was structured, I went to the internet to see what other forms of music was out there. I started driving and started traveling. I’m on the internet heavy. I’m on YouTube like it’s nobody’s business. That’s where I discovered a cat like Reggie Watts. By learning that music, I became the black sheep in the group, like ‘Here comes Masego with all that weird music.’ As a DJ, I’d put them onto it by putting the hard drums on top of all these eclectic melodies. I loved growing up in Virginia, because if I grew up in a place where there was too much of everything around me, I would’ve gotten intimidated. I pursued my own lane based on how much wasn’t around me.

You strike me as a guy who was raised by powerful women.

That’s very accurate. My mom is a real leader. All of the women in my family are just boss. When they walk, it’s like ‘Don’t talk to me unless I want you to talk to me. Are we talking money?’ The backhand is real strong. Don’t be saying nothing crazy. I have two sisters, so there was no brother to beat up on. As a result, I’ve never hidden from emotions. I have a Jamaican father who would definitely whoop you with two belts, and a mother whose hug could tear me up. She would preach the law of reciprocity to me, that how I treat someone will inevitably come back to me. I walk around with that — ‘I have to treat this person the way I want to be treated.’ I’ve gotten invaluable advice from my immediate family and the other women I know.

In listening to Lady Lady, you seem focused on presenting every side of your life.

I just try to be real. I’m a flawed human being, and I want my music to look at the whole picture. I think it’s beautiful to set yourself up to be judged for who you really are. I feel Lady Lady is a beautiful representation of where I’m at emotionally and where I’ll be in the future. I’m just as much “Black Love” as I am “Lavish Lullaby.”

What did you learn about yourself while compiling Lady Lady?

Low-key I like the boyfriend experience [laughs]. That made me realize that I need to be careful, because I was raised to be a good dude. I’m also 25 and poppin’, so I’m definitely not in a place where I should settle down. I need to make sure I’m aware of that. I’m really not ready for the relationships I’m speaking of, so this is me looking into the future. I will get that way. I’m my own OG; I’m teaching myself lessons now so I don’t have to go through it. I realize that I’m beguiling. I’m smooth and I’ve got hand tats. I don’t want to abuse my power. I have some homies who use the power for the wrong things. I hear the album and know that it’s about to travel, so I want to use my leadership properly. I’m gonna be able to be in bigger rooms, so I need to stay humble.

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Masego’s many layers