“At the beginning of the year, a mentor of mine told me that 28 was a big year for me,” starts singer/songwriter and now Grammy-nominated artist Masego. “In terms of growing as a man, thinking differently,” he clarifies — just beginning to scratch the surface of his 28th year on Earth and his sixth in the music industry.
Indeed, the fundamentals of his career and personal life are much different than they were a few years ago — he’s now adapted to the flux of an industry that leaves little space for healing with its ever-evolving, fast-paced hustle.
“[My mentor] was right – a lot of me has changed,” he acknowledges. “I was looking at my photos of me on my phone, all of the 2021 photos, and I’ve just been up to a lot of things. A lot of changes since where I started.”
It’s an understandable perspective for an artist whose initial introduction to the world came as a surprise, never planning to share music beyond an inner circle of friends on SoundCloud. In 2015, Masego released his debut project with producer MEDASIN titled Pink Polo, which featured the single “Girls That Dance” — an infectious jazz-inspired track that features trumpets and scatting, creating a distinctive mixture — with a sound Masego later coined as its own genre, ‘TrapHouseJazz.”
Pink Polo was a humble introduction to the colorful arrangement of sounds that Masego explores further in his now-Grammy-nominated project, Studying Abroad: Extended Stay — the deluxe edition of his 2020 EP. Next January, the U.S.-based, Jamaican-born singer is up for best progressive R&B album at music’s biggest night — and earlier this year, he also scored another big career benchmark as a credited producer on Drake‘s blockbuster set Certified Lover Boy, for a sample of Sego’s 2017 streaming hit “Navajo.”
Despite the rapidly changing nature of his career at the moment, though, Masego says he’s actually “kind of calm about everything. I feel like I have the zoomed out view of everything. Otherwise, it’ll probably take too much out of me. It’s a very interesting industry — I can’t even begin to describe it.” He goes on to compare his career to a video game with levels and missions — where a Grammy nomination is the final reward.
Billboard caught up with Masego just a few hours before he hit the stage in Miami, Florida (Dec. 10). The musician shared details on his new “Yamz” music video, hinted to an animation project in the works, and pondered on who he’ll collaborate with next.
There’s a lot to get into today. You are now a Grammy-nominated artist, you’ve been sampled by Drake… how are you feeling? Walk us through your processing of this insane year.
I was in NYC when I found out [about “Champagne Poetry”] and I didn’t know if I was going to be in the album or not for sure. Because at the end of the day, when we’re dealing with people at that level — they could make a decision the night [of release]. So of course, we were working on it for months. I make songs everyday that don’t make the album. I had to put my emotions in limbo and so I’m staying up to listen to the album, just like the rest of the world.
As soon as I turn it on, I hear myself — and I’m like geeked out! [Laughs.] I was like, “This is amazing!” And it was crazy. My hometown showed me so much love. It was a very great moment. I brush shoulders with a lot of high-level people, and I don’t put my emotions in it — because you don’t know what’s true. When I found out this was true, I was geeked! I was super-happy about that, happy about the Grammy — all of that.
The “Yamz” music video — it has this really unique approach, different storylines happening independently that merge at the end. What made you guys go with this type of storytelling specifically?
I gotta credit that to me being a Gemini. Whatever you would think the video would be like after hearing this 1980s/’90s vibe, I just did not want to do that. So I was like ‘First step: don’t do exactly what this song sounds like and wants to be visually,’ and also at the time, I just got this grill and I really wanted to wear it in the video, where it made sense.
I had just bought a house in Atlanta at the time and I was just falling in love with the area. I’m on a different path these days. My team tries to weave my work while I’m doing it. They were like ‘Okay. Sego, you just bought a house in Atlanta, you should shoot your video here.’ And I was just like, ‘Bet,’ because I have so many friends out here and I love to involve my people in what I’m doing. My roommate said I’m Howl from Howl’s Moving Castle. It’s this anime by my favorite director [Hayao Miyazaki], and that’s how I move in life. My team brings order to it all but the ideas i have on my phone calls and all that. I think it’s beautiful that they listen and they let things kinda happen — so they let me have fun with the video.
Japan & Tokyo specifically are inspiration points for you. There’s talk that you’ve got an animation project in the works, can you go into any detail on that?
In 2020, I was listening to and watching everything Hayao Miyazaki and became obsessed with his work, I was a fan of his meticulous details, how long he stays in countries when he’s studying a culture. He was just the dude I wanted to be one day. I started to actually implement my version of Hayao Miyazaki inspiration into my life.
I’m just taking images from all my travels and blending them together to create these worlds. I’ve met so many people, I’m just writing stories based on these people. I’ve lived a lot of lives, so now I’m just writing stories about them and I feel like when it comes to anything — you want to see yourself in the art that you consume so it’s the same thing with music. I’m making the music I want to hear, I’m making the art that I wish was already out.
Me being a fan [of Hayao Miyazaki] and Japanese culture, the writing – Korean writers are amazing as well – I feel like I want to challenge myself to ascend the level of art that I consume and of course, partner with them. I’ve already partnered with many of them, I’ve had people co-write with me in the animation field and video game field. I’ve just got a lot of interests and I’m trying them all out.
You’re certainly busy performing too. You’re about to hit the stage in Florida today, and then you also have an upcoming tour in U.K. and Europe — how are you feeling about that?
I’ll do like a small show, a bar show, anything. I enjoy performing, and I miss the small intimate performances, so I’ve been focusing on doing a lot of those. The tour is definitely going to be bringing me back to my fullest form, starting February of next year, but I’ve been performing at some festivals again and that’s been so awesome. I travelled to Mexico to go shoot that video for [“Mystery Lady (Sego’s Remix)”] — that to me is performance within itself.
I’m playing with a symphony tonight, which I think will be amazing. Because I look at myself as still building the foundation of who I want to be, but to be at the level where a symphony learns your music and takes the time, takes it so seriously – it’s kinda funny, but it’s definitely cool.
I’ve always wondered, can you enjoy traveling while on tour?
You definitely cannot. I’ve always compared the sleep you get on tours like when your laptop goes to sleep and then you just move the mouse slightly and it instantly wakes up.
My first couple tours, I got to see a lot, but it’s this flash of everything, and you don’t actually have the time to set a foundation in the places you visit. So my new journey is just finding ways to stay longer — so that’s why I’ve been buying properties everywhere like a mad man.
I’ve just been curating my tours to be able to still live life within it. It’s much better now — we’re doing all the shows, but I still have time to be a human.
You said in a previous interview that you are quite selective with your collaborations. You added two new names to Extended Stay, Sheléa & TeaMarrr. What is your recruitment process like for those?
It’s definitely me seeking ’em out. I’ve been a fan of Don Toliver’s since the [2018 mixtape] Donny Womack days, I gotta be a fan of it. I never got good at the “be fake” thing. I can’t do it. It’s either I rock with you, or you’re my enemy. [Laughs.] It’s beef or it’s love.
You really are a Gemini…
I’m a textbook Gemini! But with Sheléa, I’ve been a huge fan of hers. She’s got an incredible voice, she’s been in my group chats all the time. I’ve just been a fan. So I reached out to her, and we set time to make music, and she allowed me to put that on my album.
With Tea — I’ve been involved with Issa Rae and what she’s doing. I used to watch Awkward Black Girl in college. So to see where she’s taken her career, and anyone attached to her, just felt like a beautiful cultural moment. And Tea is mad talented, she’s got a lot of personality, she’s a little sassy. It was cool to get that energy on the project, because everybody is scared to like talk a little trash to me — ’cause I’m the nice guy — but it was cool to see a little sonic battle. Like, we’re arguing on the track — it was so fun.
I saw on Twitter you shared a few of your top songs on Spotify Wrapped. You had “Tropicana Fruit Juice” by Ycee & Bella as your number one and I believe I saw Tems up there too. My question is, if you had to choose right now, which female artist could you see yourself working with on a collaborative-style EP?
I gotta figure out who in the amapiano realm I’m about to collab with, because there’s some women out there that are like producers and DJs — I gotta find the specific names but I’m definitely headed in that direction. I love what South Africa is doing, and I would definitely do an EP with that type of energy — because every song is like a jam session, lowkey. They’re like seven minutes long and it builds up, it’s so good.
What’s been the most surprising bit of your musical career thus far?
I think people liking certain songs. I come from the SoundCloud world, where we’re just kind of making music for small friend groups, so anytime people decide to champion a song, it just always surprises me. I love all of my songs — I mean all of them, equally. I love the process of making them. I don’t even know what a hit means, I just feel like it comes down to the timing of when something drops — what the culture is doing, and then having the right person to interpret it — but it’s just too much to stress out about, so it’s always a surprise.