How Masego — With the Help of "Black Rick Rubin" Jesse Boykins III — Created His Most Personal Album Yet

Masego details the largest inspirations behind his latest self-titled album. He also tells us what musicians were pivotal to the album.

When Masego started working on what would be his recently-released self-titled album, he looked to a particular era of music for inspiration — the ‘70s. He felt that this decade’s music felt free and spontaneous: a time where artists and bands were known for transforming improvisational grooves into timeless tracks. So, Masego channeled that energy, leading jam sessions in places like Los Angeles and Huntsville, Alabama, hoping to experiment with melody and song structure without worrying about any creative limitations or pressures.

Masego is different from his last two releases. While those two projects were his attempts at expressing his feelings on heartache, love, and situationships, this one found him more assured but still searching for a forever love. The melodies heard throughout the 14-track project are also emotionally moving. For this eponymous release, he enlisted the help of Grammy Award-winning producer Kelvin Wooten and singer/songwriter Jesse Boykins III, who assisted Masego with tracklisting. With these two talents, Masego said he was able to create an album that channeled the nostalgic and soulful sounds of the ‘70s.

On Masego, it’s clear how his lyrical songwriting has shifted a bit. Paired with the sound he’s been perfecting for years (palatable ‘80s R&B from the quiet storm era injected with hints of New Age jazz, hip-hop, and soul music), the lyrics for Masego are distinct, reflective, and even haunting at times. Take for instance “You Never Visit Me,” where his syrupy vocals tell a tale of a lover that has a hold on him — even though he knows she’s never coming back.

“She would, she would visit me every winter/December is a month I give her heat, run from blizzard's east/She from under, under, underneath, she be under me/Wake up then she overseas, say she over me/Caught up? No, she got a hold on me,” he rap-sings on the single.

On previously released albums, Maesgo was deeply honest about being a hopeless romantic that was grappling with his talents. However, his latest release finds him combining that with stories of his ongoing adventures that take place as he travels, with insightful conversations he had with locals in Jamaica, Brazil, and Huntsville playing a part in his lyrics. The end result is an album that’s his most cohesive and well-rounded release to date. 

“I think the whole energy of this project was just trying to make life music — just soundtracks of my life, essentially, and other people’s lives,” he said. “I feel like all of it is just a long conversation, and then a big reflection of my journey.” 

It was 2018’s Lady Lady that gave Masego his first real taste of attention in the R&B market. A combination of love songs intertwined with soulful ballads, the album was an honest, flirtatious, and detailed look at his romantic escapades. There were standouts like “Old Age,” which found him fusing his sophisticated R&B with rap-inspired cadences; “Prone,” a lustful story about fantasies of pleasing a lover (and pursuing another one after); and, of course, “Tadow,” the sensual downtempo track that is still Masego’s most popular track to this day. 

But by the time he released Studying Abroad in 2020, it was evident that the multi-instrumentalist was still finding himself. Fleshing out his internal conflicts, Study Abroad found him yearning for the intimacy of monogamous love, only to be constantly distracted by his travels and the women he is intoxicated by at the moment. This is best captured in staple track “Mystery Lady,” where his desire for one partner is at odds with the many options available to him when he’s on the road. “But my wife be in my dreams, bruh / No, I couldn't see you / I saw her silhouette, I know I can make her wet / But when I wake up alone, 'lone, 'lone,” he sings.

With the release of Masego, it’s clear that he’s continued to grow since the release of Lady Lady and Studying Abroad. The self-titled album is a moving picture of everything that he’s accomplished since his 2018 debut, as well as a letter to himself proving that he’s leveled up as an artist. It’s a unique contribution to R&B’s current evolution, with the songs offering a masterful analysis of his personal stories and narratives he picked up from conversations during his travels, all backed by compelling song structures and delightful melodies. 

We recently spoke with Masego about his latest album, being inspired by Kendrick Lamar and Andre 3000, and what’s next for him. 

What were your biggest influences for this album?

Masego: I think it's just life. I move around a lot; I've been trying to answer some bigger questions in my life. Where am I trying to live? How am I trying to move? What do I want my legacy to be? It's heavy things, so I think as I grow as a man and a person and gather more perspectives, it ends up being in the music. I went to some interesting places like Huntsville, Alabama, and found all these affluent Black people and really talented musicians, and created a very different type of sound over there with Kelvin Wooten. So, that's a big part of the album. A lot of the DNA is in there.

Brazil plays a big role just because of how my voice sounds to their culture. We have Bob Marley in Jamaica but they have Djavan, and I am adjacent to some of those cadences and melodies. I spent a lot of time out there exploring that. And you notice when you go to different countries, it's a very similar structure when it comes to the Black community. You got the hood, the rich people, the people that are chilling with the rich people. You got this and that. When I start to zoom out and look at the similarities everywhere I go with Black people — with love, business, the hustle, all that — it creates an album.

Were there any other influences?

I spent a lot of time in nature doing this album, and seeing how we mirror nature and plants. Mind you, none of this involves a mushroom trip or anything. I'm just walking outside and just saying, "Yo, that's crazy." 

How did you approach tracklisting and naming songs?

I had a lot of help choosing track titles and the track order because of Jesse Boykins III. He’s a genius, he’s like a Black Rick Rubin to me. I think the questions he asked me and the conversations we had in his studio, that was a huge part of the album that made choosing the intro a lot more obvious. It's like, "Oh, OK, look at these lyrics and look at these feelings and emotions and textures." I answered my own question after talking to him, and that's how it goes. At first, there were so many versions of this album. It's crazy.

So it sounds like you had about 150 songs, and then you had to break everything down?

Yeah. And the thing with it is, I could say a similar thing with five songs, but it's just deciding how I want to say it and will people understand it with this one? How much do I care about that? So, it's mad talking and listening. But making music is not hard; creating a song, that's not difficult for me. It's just piecing something together to make sure you get out of your own head and think about how a regular person walking around is going to hear and receive this. That's the difficult part, stitching something together properly.

Did you give yourself space to live and grow as you worked on the album?

Yeah. [You’ve got] to give yourself grace because there's no manual of how to make an impactful album properly, or how to approach your own career. You can look at things but you have to do a lot of deciding and being very intentional about how you want to go about it all, and knowing that every song is like a house and it goes up and down in value. There's so many things you have to think about in that your albums are homes, where so much can live in it, so many people can be served by it, and so many people can experience it. So, you gotta take time to build your house. And a lot of it is just experiencing life, which is the foundation of that house.

I don't mean to keep preaching about metaphors and things, but I can't approach it the same way as other people. I've seen the whole, "Yo, we rented a studio out for a week, this is what we're doing." But that's not my process. I feel like I gotta be around people for real and talk to people and get very vulnerable, which is not my favorite thing to do. But you have to do that to actually have depth in songs. You can't cheat Black music; you can't cheat the whole R&B soul. It's either you're doing it and you live it and you are it, or you were just cosplaying it. I don't have interest in cosplaying it.

Was there a goal with this self-titled album?

I really want to make my albums like some good wine. I just want people to sleep on it a little bit, and then month five they're like, "Yo, track five." I get a kick out of that where you can find a lot of things to pull from the songs. Maybe it's background noise for the first listen, maybe you just like the singles for the second, and then maybe, "Oh wow, I peep this now." I love artists like Kendrick [Lamar] that leave us with so much to pull. J. Cole leaves us with so much to read into and, of course, Andre [3000]. I aspire to do things like that where, for years, you can just take a college course and pick apart some decisions made in the album.

What’s next for you?

Learning how to cook more, that's the move right now. But other than that, I just got a lot of business ventures trying to step the pockets up so I can do some grander things. So, spending a lot of time overseas, a lot of time with Jesse Boykins III. Honestly, he's really helping me understand business in a deeper way. I'm looking forward to just leveling up the business so I can help other people craft a world for themselves.