TOBi is having his moment. In the last four months alone, the Nigerian-Canadian singer-songwriter has been name-checked by the likes of Snoop Dogg and Jamie Foxx, and invited to Los Angeles to work on music with The Game. (“My fans are now your fans,” the Los Angeles-raised emcee posted on Instagram.) Add to that the release of STILL earlier this month — his debut full-length project under Same Plate Entertainment/Sony Music — and 2019 has shaped up to be quite the year.
“I’m where I’ve wanted to be for so long,” says the 25-year-old artist, born Oluwatobi Feyisara Ajibolade. “The last four months has been a period of exponential growth.”
Born and raised in Lagos, Nigeria before he moved to Canada at the age of nine, TOBi’s earliest works found a home in a notepad his mother gifted him.
“I used to write everything. I’d write stories, fictional tales, songs, poems,” he says. “My mom gave [it to me] before I left Nigeria. So I had that with me. And I would just write everything in there.”
Early on, his musical influences ranged from DMX to Lil Romeo. His older cousin introduced him to the former’s music; he played the latter in a school production at the age of six or seven.
“My mom gave me a notepad before I left Nigeria. So I had that with me. And I would just write everything in there.” – TOBi
“I had the whole attire down and everything,” says TOBi. “The durag and the oversize t-shirts.”
At nine, he left Nigeria with his father — arriving in Canada before the rest of his family could join them. He was chosen to go first, he figures, because he was the “low-maintenance” one of his siblings. At first, they stayed in Ottawa, then moved to Toronto and eventually Brampton. All the while, TOBi waited for the rest of his family to arrive.
“[My Dad] was working so much. He had like two jobs, so I rarely saw him for that first year,” says TOBi. “I didn’t want to be here, so I spent a lot of time with myself writing.”
There were the early struggles. Body language, and unfamiliar expressions, and the isolation that comes with being separated from home.
“The little social nuances, I didn’t understand any of that,” he says. “I would argue until this day, I still grapple with certain things.”
In high school, TOBi wrestled with anxiety and what he describes as “different mental health issues.”
The first year and a bit was very difficult. I didn’t want to be here, so I spent a lot of time with myself writing. At the time I didn’t know, but it was me coping, self-soothing.” – TOBi
“I couldn’t even contextualize it, because I didn’t know the language,” he says. “Part of that was going through counselling, therapy, getting some work and understanding what was going on. And a lot of that was self-directed until I found somebody who was able to guide me through it.”
His first time performing music, it was in front of his tenth-grade classmates. For a civics project — the Youth Philanthropy Initiative — he had to profile a non-profit organization.
“I did one for Victim Services of Peel. But my presentation was a song,” he says. “And that was the first time I ever performed music for a group of people. And I won the whole [contest]. It was lit.”
After high school, TOBi studied biology and psychology at Wilfrid Laurier University in Waterloo, Ontario. For his family — as is the case with many first-generation Canadians — post-secondary education was expected.
“It’s been instilled in me since I was a fetus,” he says.
He completed his degree, but struggled with doubt throughout his time at Laurier.
“I just kept picturing myself as an older version of me,” says TOBi, of his studies. “Like, am I going to enjoy what I’m doing?”
“I just kept picturing myself as an older version of me. Like, am I going to enjoy what I’m doing? That picture wouldn’t leave my head. And that happened the whole undergrad. Literally the whole undergrad. It was cemented in my mind.” – TOBi
His first big musical break came in 2017. A song he wrote as a demo — one he wasn’t sure if he would even release — landed on HBO’s Insecure. In the meantime, TOBi worked in mental health, both as a youth engagement coordinator and on a crisis line for those in distress.
“Man, the crisis line changed my life,” he says. “I learned that everybody has their own worlds and paths that they need to traverse.”
It was also 2017 when TOBi started crafting STILL. Over the next two years, the project would grow into thirteen songs, with production from the likes of !llmind (Kanye West, J. Cole, Ariana Grande) and Arthur McArthur (Drake, Rick Ross, Big Sean).
“It almost felt like I had all these stories and ideas in my head that I had no choice but to get out,” he says.
Now that the album is out, complete with a billboard at Toronto’s Yonge and Dundas Square, TOBi can enjoy the fruits of his labour — including the shout-outs from Foxx and Snoop.
“All those mixtapes that I was doing, all those writings, all those songs that I made for 20 people to hear,” he says, “it wasn’t in vain. It was a set-up for bigger and better things.”