Now Reading
A conversation with Masego: “If you see me with a fruit tree, I’m gonna cry”

A conversation with Masego: “If you see me with a fruit tree, I’m gonna cry”

Masego is one of those rare breeds whose talent only a handful of people of each generation can match. He’s a musical force of nature and self-proclaimed sex symbol with an impeccable stage presence. I got the chance to interview the 6’2*, Jamaica-born, Virginia-raised, multi-instrumentalist before his show in Stockholm this October – an interview I was particularly excited about because I’ve had Masego on my radar ever since he dropped his first Pink Polo EP in 2016.

Full disclosure, Masego has been one of those names I’ve kept up my sleeve whenever I’ve tried to impress a guy with my great taste in music. Because once you’ve come across the Masego TrapHouseJazz sound, you’ll instantly become a fan and you’ll instantly love the person who introduced you to him. With this being said, proceed with caution because Masego concerts might just end up being a minefield of guys you used to date. But that’s neither here nor there because rest assured, a Masego concent is well worth the awkward impromptu rendezvous with your ex. 

A few minutes before Masego stepped on stage to blow us all out of the water with his performance, we sat down in a rather chilly room to discuss what his parents, who are both pastors, think about the twerk videos in his DMs. I also attempted to psychoanalyse his love life after interrogating him about his relationship with his mom and giving him a rundown of his zodiac sign characteristics. Because why not get down to the nitty-gritty of it all when I had the chance?

Before I left we snapped a couple awkward pictures in which we both blinked and he asked me if he should wear sandals instead of Jordans for the show. I asked if he can dance in sandals. He said yes, so sandals it was.

How are you feeling today?  


I want to know how you are doing physically, spiritually, and emotionally in life right now.  

Okay, we can get deep! I’ve got both sides to me! Physically… I think I went a little too hard on stage yesterday. I did some extra things, tried some new dance moves. So yeah, physically I’m tired. But I played basketball for many years so I’m always down for the game.  

And how are you emotionally and spiritually?  

I just watched this interview with Oprah being interviewed by a Stanford student and it was the most beautiful thing ever. She was just talking about how it’s your job to fill yourself up. Because as a giver, I give to hundreds of people every night. So it’s cool if I get a massage, it’s cool if I pig out and get some crazy vegetarian food that costs a lot. I feel like sometimes in the past, I would just go through the emotions so I could check them off the list. But more so nowadays, I’m trying to fill myself up with things that make me feel good.  

Alright so you’re doing good is the ultimate answer to my question?  

Yeah. I mean, I’ve got to make checks every once and again that I still feel. But it still works out pretty well. It’s kind of hard to sing a song like Navajo because it was a hurtful time in my life low key. But to be able to revisit it for like four minutes genuinely and then snap back out of it, it’s quite the feat.

Tell me more about that experience.

To be able to jump in and out of real stories in my life, and then go back and be a normal person is ridiculous. It takes me like 20 minutes to calm down after the stage. I can be anything after a show. I might be too cocky, mad about something, pimpish… It takes a while to snap out of that. Cus’ I mean, I’ll perform anything from Pink Polo to Loose Thoughts to Lady Lady, to whatever else I make up on spot. And I’m just jumping into different times in my life, like time travelling. And it’s so interesting to just mentally go there. Because I’m not here to just perform and be a robot. I want to literally show you who I was when I made that song. So I jump into that guy, then jump out of it.

I feel like with Lady, Lady you’re moving away from the trap and house part of your genre TrapHouseJazz, and moving more towards jazz. Has that been a deliberate decision?  

I think it was natural, honestly. I feel like when I freestyle, whatever music I’m making is just how I’m feeling. So I think naturally when I was 18 I was black boy joy, I was Pink Polo, one hundred percent. And nowadays, I’m just 25, trying to get this beard to connect, and sonically, that’s what it is.  

Trapp House Jazz started out as a genre but it’s more so a mindset. I approach everything with ignorance meets elegance. Classy, but reckless, you feel me? I say “you feel me” a lot, I’ve got to stop. Anyway, trap house jazz is like a mentality, you feel me? Darn, I’m still saying you feel me!  

It seems like there is this ongoing theme in your life of a clashing of different lifestyles that you summarise in one of your Instagram captions: “On the other hand I battle with lust, being rapperish with my spending, belief in the validity of a monogamous relationship as an entertainer and being kind for kindness sake”. And I’m thinking that growing up with religious parents who are both pastors, and then living the life of a touring artist, those two worlds must really clash? Would you say that’s an ongoing, internal conflict in your life?  

Yeah, and I think it’s a real thing that you have to – “you” being me – have to embrace and emit to. Because I didn’t want to become “the gentleman guy”. It’s too much pressure. Then you’re Stephen Curry; everybody thinks you’re the nice guy until you throw your mouthpiece. I wanted to make sure I was honest. If you want to love me for being this perfect gentleman, just know the other side of me. And if you still love me? Beautiful!  

Is this something you said to your parents or to yourself?  

Okay not straight to my parents. I’m not that strong! Like, “alright mom! If you want to love me… love my trap side!” Nah, I couldn’t say that!  

So how do you go about that? Because from what I can understand, you don’t really curse, you don’t drink… or do you?  

If you catch me on the right day I’ll sip some wine. And the n-word and hoe happen a lot in my life. So if you consider those curse words, I’m just as bad as the next guy. Honestly, I don’t have the desire to curse. I say mother trucker a lot. And if you read it on paper, it’s like, “this dude’s corny.” But then if you hang out with me it’s like, “wow, now I’m saying it too.”  

It’s an ongoing conversation with my parents. Because my father is on one side of things. He wasn’t a pastor at first. He was in Jamaica and didn’t believe in religion for a very long time, and he grew into who he is today. My mother? Church. Forever. That’s her lifestyle and that’s her upbringing. The last conversation I had with my mother, I was saying: “think of me as a musical actor where good acting is all the characters that Will Smith has played. Even though he’s not an alien slayer, there’s an element of it that’s so believable. There’s some truth in here, and then there’s some made up, hyperbolised elements.” And I feel like that’s what the album is as well. I wasn’t on the drank and the weed even though I said I was in Prone. That was from a dream that I had where I was embracing that lifestyle. And, even in Lavish Lullaby I say, “Tryna not go Cobain, just turned 27.” I’m 25. So I think that’s the way I find that compromise.  

I’m like, mom, it’s not as bad as you think. If you read it word for word, it might hurt you a little bit, which it did! She doesn’t like certain lyrics off the album. She doesn’t like me having women with their booty out in my music videos. I get it. But it’s an ongoing conversation because I’m staying true to me, ‘cus I like twerk videos. I’m southern. I like hips and women. But at the same time, I’m super respectful to my parents and I’m super communicative to them.  

I feel like some of my peers, like my friend Juice, I was like, “dude, you’re talking about hitting hoes and crack and cocaine in your songs, but what does your mom feel?” And he goes: “my mom’s worse than me.” So everybody has their own balance.

What does the ultimate day look like for you?

There’s definitely got to be a chef involved. We have a jam session in multiple rooms. There’s a fruit garden. If you see me with a fruit tree, I’m gonna cry… and what else is involved? Some type of outdoor adventure, that could be cool. It should probably end in a massage, like a professional one. Probably like a cartoon marathon, like some old ones. And then a cry-laugh. If I’m cry-laughing, that’s a day! If there’s a lady involved that would be cool but just for the conversation, because I think until I’m in love, I’m just dangerous to people.

I looked up the characteristics of a Gemini and it seems you’re a textbook Gemini!

Ooh please read them because I always forget them until someone tells me!

You have an ability to learn quickly and exchange ideas. Geminis are sociable, passionate, dynamic, curious and ready for fun, with a tendency to suddenly get serious, thoughtful and restless. Geminis are in love with love, and they adore the ritual of it all. And a Gemini could spend a lot of time with different lovers until they find the right one who is able to match their intellect and energy. They need excitement, variety and passion, and when they find the right person, a lover, a friend and someone to talk to combined into one, they will be faithful and determined to always treasure their heart. Geminis can also be two-faced. They’re known to stir up gossip just to keep things exciting.  Is that true?

Yeah! My lies are phenomenal.

So you really are a textbook Gemini?

Yeah! You know what you’d be getting into. I tell women, read it! That’s me!

Are you a heart-breaker or do you usually get your heart broken?

Nah I think I’m a heartbreaker. Because I’m like a stone. If you get to me? Then you get a song. But most people can’t get to me because there are so many shells.

But don’t you think that’s like a defence mechanism right now because you know that it wouldn’t be realistic for you to settle down? So your entire system is making sure you don’t, really, seriously, fall for a girl.

Yeah, because honestly, people kind of like don’t know what they’re getting into. I’m definitely a nice guy but my life is a lot to handle. You have to be a very secure person just to deal with the extra stuff that comes with me. Because, like I said, I’m an old man. Me and my shorty, it’d be just us. I’m very focused on just one person at a time. It would be an incredible life for us but the things around us you’d have to learn how to tune out. I can tune it out so easily. But the average person can’t. So the defence mechanism is for the woman’s own good. I’m charming as a mother trucker. Which is bad. A heartbreaker! You heard it here first!

Interview by Michelle Hallström

Scroll To Top