How Masked Wolf Went From Underground Sydney Rapper To Global Superstar

What you know about rolling down in the deep?

I’d bet we all have some sort of take on it. It could take you back to 2011, when Adele’s ‘Rolling in the Deep’ reigned supreme; perhaps if you’re some kind of adventurer, it evokes a particularly bad night spent on a ship; or maybe you’ve been there yourself, dizzied and disoriented as the world pulls you under. Right now, however, the phrase belongs to but one man — Sydney emcee and global hitmaker Masked Wolf.

It was 2019 when sales representative and aspiring emcee Harry Michael staked his claim, those raw bars — “What you know about rollin’ down in the deep?/When your brain goes numb, you can call that mental freeze…” — being a vivid account of the dispossession he was feeling.

“I think the biggest hurdle and the biggest obstacle I’ve found was just getting my name out there and getting any type of recognition,” he tells me at the start of a busy day. “That was a really hard mental struggle for me, because when you feel like your music has potential and people don’t accept it, it hits you on the head a bit.”

Still, Harry held strong — he hunkered down in his home studio and continued to hone his pen on the edges of his nine-to-five. It’s one he’s been sharpening since the distant days of high school. “When I was about thirteen, fourteen, my parents got divorced,” he divulges, honest and frank. “I wasn’t a very talkative person in a sense of my feelings — like I was a very talkative and social person in general, but I was very good at wearing a mask and acting like I felt okay.”

“That’s when I started writing and expressing how I was feeling, and then it became songs from that,” he explains, childhood favourites such as Eminem and 50 Cent giving way to artists like Hopsin, Kevin Gates, and Joyner Lucas. “They’re all very rapid, aggressive when they want to be, but they speak about things that are on their chest, and that’s what I always wanted to be.”

Their assertive, unblinking honesty a powerful touchstone, Harry folded elements of alternative and indie rock into his sound, wielding vocal hooks as powerfully as he does intricate verses. “That’s what I envisioned,” he says. “This mysterious guy that can sing, but when he wants to rap, it just comes out of nowhere and slaps you on the nose.”

Astronaut On The Charts

That’s certainly the case on ‘Astronaut in the Ocean’, which seamlessly segues from the earworm melody to the rapid-fire bars. Masked Wolf bites with surgical precision, his sharp inflection cutting through the spacious mix.

“It was always hard to tell people that I was a rapper, I’ve never really said that to anyone,” he says, his 2018 debut ‘Speed Racer’ a culmination of years of refinement. “I just wanted to write music and express my emotion, but it took me about 5 to 10 years just to find my sound and actually talk about it in songs.”

It mightn’t have been the beginning, but ‘Speed Racer’ sure was the beginning of something. “Getting that dark vibe was pretty hard, but we nailed ‘Speed Racer’,” explains Wolf, putting his relationship with producer Tyron Hapi down to a mix of mutual talent and hard-earned understanding. “You can see as songs were released, the sound became better.”

“That’s what I envisioned…This mysterious guy that can sing, but when he wants to rap, it just comes out of nowhere and slaps you on the nose.”

And it did: ‘Vibin’ threw a spotlight on his jagged rapping chops while ‘Numb’ indulged his knack for arena-scale anthemics — and ‘Astronaut in the Ocean’ was the ultimate synthesis.

Just in case you’ve never gone seriously viral on TikTok — and few have reached Masked Wolf’s dizzying heights — Harry describes it as “kind of like when you walk into a news agency and they tell you you’ve actually won the lottery.”

It’s not hard to see why the track took like wildfire — but even with his healthy self-belief, Harry says it was legitimately surreal. “I saw it all from the start, because I was the one going to every single TikTok video thanking them for using my song,” he admits, still just as appreciative, “I’ve been there since 1000 videos, 10,000 videos, 50,000.”

That those numbers are such prized achievements speaks to Masked Wolf’s humility; the song itself has now featured in well over three million TikToks. It’s fuelling workout tutorials, scoring dog walking clips, lacing slo-mo sports highlights and folding into all manner of sketches, each new invocation a show of versatility.

It’s not just a manner of what it’s scoring, but who. “Obviously Patrick Mahomes was crazy, but I’m not a massive NFL fan,” he tells me, grateful all the same. “The JLo thing to me was massive, and not just because she’s JLo. It was because it was a TikTok where she was like, ‘okay, I’m going to use this sound and this song to dance to.’”

The more Masked Wolf elaborates, the clearer his motivations become. “The Shazam thing [he’s currently the #2 most Shazamed artists globally] will always be the biggest achievement,” he says, eschewing Billboard chart placements and powerful cosigns. “I say to everyone, people that Shazam, they hear something and they’re like, ‘I need to know what this is right now’.

“For someone to pull out their phone randomly during their day and be like, ‘I need to know what this song is, tell me right now’… it tells me I’ve hit the nail on the head, and I was right about more ears getting in touch with the song.”

Vindicated though he is, Harry’s recent successes have eclipsed all expectations — he’s now one of the world’s most-streamed artists. “To be honest, I was happy with 20 million streams,” he says, that major milestone now a drop in the ocean. “I went out with 10 of my best mates and celebrated 20 million streams because I was super happy with that achievement. It’s a weird thing, but I never ever celebrate my birthdays, I celebrate my achievements.”

It seems there’s more cause to celebrate with every passing day, but Harry’s hard yards have sown diligence and dedication. “I’m just going with the flow, because my mental has always been used to grinding and my physical has always been used to work,” he says. “It’s trying to keep pushing myself and knowing that I haven’t made it yet, it’s just that the opportunity’s there.”

That’s a chance he intends to seize — he’s currently “working on a lot of new singles” and returning to his newly-refurbished home studio to work on his debut album.

“The album is going to be absolutely nuts,” he promises, teasing a mysterious international feature. “I’ve been trying to vibe off My Beautiful Dark Twisted Fantasy, just to get some motivation from Kanye, but I’m keeping this in the Masked Wolf category,” he says, holding firm to his longtime producer Tyron. “He’s solo producing my album… he knows what I like and what I’ve done, now it’s come to a point where he just knows me because we’ve been together so long.”

And with an international hit single under his belt, Harry is aiming very high. “It’s going to be based around astronomy,” he explains, adding he’s planning on sharing it “hopefully by the end of the year or the start of next year.”

It might seem like a wait, but Harry’s well aware that patience is a virtue. In staying his course and trusting his process, the record looks to be an opportunity for the world to get to know Masked Wolf — both the man and the beast. “I kind of see it as the werewolf transformation, and that’s what I always based it on,” he muses on his mantle. “I’m just a normal person, the full moon is the studio, and when I get into the studio, the transformation happens.”

As his days grow busier still, Harry can feel like “Masked Wolf from the start of the day to the end of the day,” but there’s no Mr. Hyde without Dr. Jekyll. “I’m very chilled out,” he tells me of his regular day-to-day. “I never talk about my music. I never boast about it.” Think of it like a “Bruce Wayne that turns into Bane.

“I’m a different person, and then when it’s time to do music? It’s time to do music.”

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Conor Herbert is a freelance music writer who has written for Pilerats, DJBooth and more. Catch him on Twitter.