Masego on How Women Inspired His Debut Album 'Lady Lady' & His Dream Collaborations

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Masego has been perfecting his artistry since his college days incorporating the instruments he learned to play in his youth -- saxophone, drums, piano -- into beats and playing around with vocal loops. After releasing The Pink Polo EP in 2016 and Loose Thoughts EP in 2017, the Virginian rapper/singer/multi-instrumentalist recently dropped his debut full-length album, Lady Lady.

“I think this album means coming age,” the 25-year-old explains. “My previous projects have different energy, and I feel like I’ve graduated to a more mature version myself -- my beard’s almost connected, my man body’s comin’ in.”

“Some it is future talk as well,” he adds. “I haven’t experienced my wedding day, but I have a song called ‘Black Love,’ which is exactly that.”

Lady Lady is a culmination Masego’s influences and experiences. He blends elements hip-hop, R&B, jazz, dance and even comedy without it feeling forced or strained, and recruited the likes SiR, FKJ and Kehlani, among others, to collaborate on the album. Having just wrapped up a few tour dates supporting Leon Bridges, Masego is gearing up to embark on a massive headlining tour throughout Europe and North America.

While on his way to the Berkeley stop his Leon Bridges tour, Billboard caught up with the self-described “TrapHouseJazz” artist to talk about the debut album, what to expect from his headlining tour, and why women are his biggest inspiration.

Your debut album Lady Lady came out today. How does it feel to have it out in the world?

It feels like silk pajamas, straight from overseas.

As the title implies, women were your main inspiration for this album. What specific women have inspired you throughout your life?

It all starts with my mother. She was the music director at my church, so she was the one putting me on to old gospel music. I’ve been a momma’s boy forever, so that’s how the whole charming situation developed growing up — I’ve got two sisters as well.

Next was my substitute teacher in middle school. As the story goes, she came into class with a binder, and on the binder was a picture Najee Davis, the saxophone player. I had this crush on her, so I just put two and two together and was like, Okay I gotta play saxophone and then she’ll love me and we can get married. So yeah, when I was young I chose to learn how to play the saxophone, and I became obsessed with learning. I took swimming lessons so I could get my lungs stronger; every Sunday, I was practicing sax. I got first chair and all that stuff. She course went away, because she was a substitute teacher. But she was the first woman to really bring out the best in me — she made me work hard, she made me try to be the best that I could be.

In high school it was this girl who put me on to Jamie Foxx’s standup Out the Foxxhole. That was a big deal to me because it was the first time I saw someone being the funny man but playing keys as well. I really cite that as a big deal to me.

In college, this cheerleader put me on to this artist called Kimbra, and that was huge to me because that’s the first time I saw somebody looping. She sampled her voice and made a song with that, and that just blew my mind. It’s a beautiful journey. Every time I have a conversation with a woman, I gleam something from it.

What is it about women that draws you to them more than men in regards to inspiration?

I think it’s a level emotional vulnerability. I’m Jamaican, so I come from a very whip with two belts background — being sensitive isn’t really part my culture. When I get around women, they’re down to talk about how a piece art made them feel, or anything that they’re feeling in general.

Every time I talk to women, it can be about how nerdy I am about a certain keyboard player or a certain song, or these chords. But my homies — I played a lot sports, so we talk about how long you can play basketball with your leg broken. laughs] I think both sides are necessary, but as far as influence on my creative side, the conversations I have with women, there’s something special about them.

You call your music “TrapHouseJazz,” which is an accurate description what you do — you weave so many different genres into this album. Do you ever find it difficult to cohesively incorporate such a myriad sounds into your work?

I think it’s such a natural blend, because all the travel I do and music I listen to takes an effect on me, so when I’m freestylin’, having a jam session, all these things kind mesh in one. I was on Twitter this morning, and a girl described my music as “skirt skirt jazz” laughs] because I’m taking that little trap element and really putting some sophistication on it. I love when people are trying to understand what the music really is. They know they love it, they’re just trying to figure out what to call it.

But it’s been natural for me. I’m not with this scientist coat on really mixing genres like that. I just feel like I live life, and then whatever comes out in the next jam session is what it is.

So it’s more a subconscious choice than deliberately trying to incorporate all your influences?

Definitely. I remember when I was very young, I tried to make a calculated recipe. I was like, Okay, I’m gonna have a J-Cole-ness with a little Andre 3k, mix in some Tito. But I could never make it happen because I was like, This is just too much to think about. Music is just something I do.

You cite a lot interesting musical influences, but to me the most intriguing is ’30s big band leader Cab Calloway. How would you say he inspires you?

My grandfather gave me a Cab Calloway record, and when I was in high school I found this documentary on him. His spirit — from the joy that he has conducting music to the way that he dresses with his Parisian scarf and his German trousers and South African shoes — was just embodying the fullest form me. The call and response was beautiful. The spirit him was very familiar. I cite him as one my musical fathers.

There are a number features on Lady Lady. Who’s on your dream collaboration list?

I think for the culture I gotta collaborate with Pharrell. He’s from my area, that’d be amazing — what he would pull out creatively. If Andre 3k would take a break from his walks in New York, I would definitely collaborate with him. I’d take a picture with him too, but if he wants to collaborate I’d love that, too. Me and H.E.R. should definitely make a song. She’s the real deal as well.

You’re currently supporting Leon Bridges on a few tour dates. How’s that going?

I think this tour is special because I get to release the comedian side me. They’re really large crowds, so they come with the I want to be entertained mindset. So I get to meet them for the first time, I’m jokin’ on people, we’re having conversations and inside jokes. It really feels like the Jamie Foxx standup I watched in high school. I’m enjoying it.

After that stint is over, you’re going to UK to embark on a massive European/North American headlining tour. What can fans expect from your live show on that tour?

My shirt f — they can definitely expect that. Imma be feelin’ myself on this tour. A lot silk and jewelry and sweat.

And sax!

Oh yeah, I’ll bring that.

I haven’t seen you live yet, but I hear you put on a pretty good show.

I’ve been to a million shows, so what I wanted to do is combine the best pieces my favorite shows. And I feel like everybody should get a different version, so if you follow me on tour it’ll be a different version in each city. I feel like people deserve that.

What’s the next chapter for you?

I think jam sessions, for real. That’s where it always starts. I’m sure this tour alone will inspire so much, so I feel like getting in the room with some musician friends and just takin’ it back to day one.