For over a decade, Drake has represented Toronto to the world.
But long before the global fame, platinum albums, and sold-out stadium tours, the city already had cultural architects building the foundation of hip-hop.
One of the most fascinating—and least talked about—names in that story is Big Apple Hozea Massiah.
Drake & Big Apple: The Untold Toronto Story Behind the “I’m Not A Rapper” Movement.
Toronto hip-hop history is full of hidden figures—people who shaped the culture long before the world started calling the city “The 6.”
One of the most fascinating names in that story is Hozea Massiah, also known as Big Apple—an entrepreneur, cultural visionary, and streetwear pioneer whose influence touched music, fashion, and media across Toronto and beyond.
And if you’ve followed Drake closely over the years, you may have noticed something interesting:
The Big Apple connection keeps appearing.
From early Toronto hip-hop circles to cultural shout-outs and fashion influence, the relationship between Drake and Big Apple has become a topic of intrigue among fans who want to understand the deeper roots of the city’s rap scene.
Let’s take a deep dive.
The Man Behind the Movement: Who Was Big Apple?
Before Drake became the global superstar known as the 6 God, Toronto already had cultural architects shaping the hip-hop ecosystem.
Big Apple was one of them.
Hozea Massiah built his reputation as:
- A streetwear innovator
- A media creator
- A mentor within Toronto’s hip-hop culture
He created several influential brands and projects including:
- “I’m Not A Rapper”
- DRÜGS (Do Right U Gain Success)
- Hip Hop Don’t Know Ü
- Big Apples World TV
These platforms promoted emerging artists, fashion, and hip-hop culture long before Toronto became globally recognized for rap dominance.
In many ways, Big Apple represented a generation that helped build the foundation Drake would later take worldwide.
Drake’s Toronto: The Culture Before the Fame
When Drake began rising in the late 2000s, Toronto hip-hop was still fighting for recognition.
New York dominated.
Atlanta was exploding.
Los Angeles had legacy.
Toronto?
Still proving itself.
That’s where figures like Big Apple mattered.
He was part of a movement that:
• Hosted events
• Promoted artists
• Built fashion brands tied to hip-hop identity
• Created media platforms showcasing the scene
Through projects like Big Apples World TV, he interviewed emerging talent and documented the culture.
In other words:
Toronto hip-hop had storytellers before it had superstars.
The “I’m Not A Rapper” Shirt: A Statement That Became a Movement
One of Big Apple’s most iconic creations was the “I’m Not A Rapper” brand.
At first glance, the phrase sounds ironic in hip-hop.
But the meaning ran deeper.
The idea represented people who lived hip-hop culture without needing to be rappers themselves.
Entrepreneurs
Designers
Promoters
Creators
People who built the culture behind the scenes.
The brand eventually became a recognizable piece of streetwear connected to the Toronto underground.
And that’s where the Drake connection starts raising eyebrows.
Drake & Big Apple: The Mentions Fans Talk About
Within Toronto hip-hop discussions, there have long been claims that Drake referenced Big Apple in songs and conversations over the years.
According to interviews in the Toronto hip-hop community, Big Apple himself spoke about Drake mentioning him multiple times in music.
For fans who analyze Drake lyrics the way sports analysts study game tape, this has become a fascinating rabbit hole.
Because Drake has always been known for:
• Referencing real people in his life
• Paying homage to Toronto culture
• Embedding subtle shout-outs in lyrics
Which makes people wonder:
How deep does the Big Apple connection really go?
Streetwear, Status & Drake’s Fashion Influence
Drake has always had a powerful relationship with fashion.
His influence helped make brands explode overnight.
Think about:
- OVO
- Nike collaborations
- Rare vintage jerseys
- Toronto sports culture
Whenever Drake wears something—even casually—it can instantly become a collector’s piece.
That’s why sightings of Drake wearing niche streetwear or underground brands often spark intense interest among fans.
Because in hip-hop culture, clothing isn’t just fashion.
It’s a message.
The Legacy of Big Apple
The hip-hop community mourned the loss of Hozea Massiah in 2025, recognizing his impact on culture, fashion, and entrepreneurship.
Tributes described him as:
• A mentor
• A visionary
• A cultural connector
His influence stretched far beyond Toronto—from New York to Los Angeles and Atlanta.
And perhaps most importantly:
He represented the entrepreneur spirit behind hip-hop culture.
Could Drake Reference Big Apple Again?
Drake is known for doing something unique in music:
He documents his life and environment through lyrics.
Friends.
Mentors.
Enemies.
Cities.
Moments.
Everything becomes part of the story.
With rumors swirling around upcoming projects like Iceman, fans are already speculating about what cultural references could appear.
Could Big Apple be mentioned again?
Could there be a tribute?
Or even something bigger?
A Future Collaboration?
In hip-hop, the past always reconnects with the future.
Legacies evolve.
Stories continue.
And sometimes, cultural figures who shaped the early scene finally receive global recognition years later.
That’s why fans are asking a bold question:
Could Drake and Big Apples World collaborate one day?
A tribute capsule collection.
A lyric reference.
A cultural documentary.
Or something even bigger.
Because when you study Toronto hip-hop history closely, one thing becomes clear:
The roots of the culture run deeper than most people realize.
And Big Apple was part of that foundation.
Final Thought
Drake may be the biggest artist to ever come out of Toronto.
But every giant stands on shoulders.
Promoters.
Entrepreneurs.
Visionaries.
People who believed in the culture long before the spotlight arrived.
Big Apple was one of those people.
And if you’re a true Drake fan who wants to understand the real story behind Toronto hip-hop, then the name Hozea Massiah is one you should never forget.
Drake may have taken Toronto to the global stage.
But every movement has people who helped build the culture before the spotlight arrived.
Big Apple Hozea Massiah was one of those figures.
And as more fans dive deeper into Toronto’s hip-hop history, his name continues to resurface—reminding the world that the story of the 6 is bigger than any one artist.