Leaning back in a wooden chair in Toronto’s east end, one hand resting pensively on his chin, Daniel Caesar untangles the series of events that got him to where he is today.

The soft spoken Oshawa native, born as Ashton Simmonds, has a lot to be proud of.

From the release of his debut full-length album Freudian – an R&B love letter tinged with gospel – to an American late-night talk show performance with one of rap music’s current elites, Chance the Rapper, Caesar seems to be on an endless climb upwards.

Last week he claimed not one but two Grammy nominations for Freudian – perhaps the icing on the cake.

“It’s still sinking in,” he said with a grin. “We were on the runway on a plane about to go on the last leg of the tour. We kept refreshing our phones and trying to get the list. One of my managers eventually caught it and we made a big ruckus on the plane.”

His manager and producer, Jordan Evans, who sat watchfully nearby, made Caesar’s account of hearing the news seem modest.

“We announced it to the plane and everyone applauded,” Press said. “We got hugs from flight attendants.”

Daniel Caesar
Daniel Caesar sits inside The East Room, an artist space in Toronto's Riverdale neighbourhood, where he has performed, shot music videos and, at one point, lived in. (Rachael D'Amore)

The accomplishments will continue to pour in this weekend when Caesar starts the Toronto leg of his international tour with five consecutive sold-out shows at the Danforth Music Hall. For any artist, it’s a huge feat.

For a 22-year-old who, just a few years earlier, left his family home in Oshawa, worked grueling late nights at a downtown Toronto restaurant and couch surfed to get by – the sight of his name on the Danforth’s marquee “surpassed expectations.”

Standing outside the Danforth Music Hall one week before his marathon of shows, Caesar motions toward Broadview Avenue where once lived and made music with Evans. It was there, in Toronto’s Riverdale neighbourhood, that the fabric of Daniel Caesar came to fruition.

“Jordan and I used to live down the street on Broadview Avenue. Whenever we’d come to grab late night McDonald’s we’d pass this place and talk about how, in a few years, I’m going to play that venue. And now we’re doing it… we’re doing it five times,” he says.

“It’s going to be very emotional for me because it’s speaking things into existence. Everything we dreamed of is becoming a reality. So I’m going to lay it all down, give them it all.”

Daniel Caesar
Daniel Caesar stands outside The Danforth Music Hall where he's scheduled to perform five consecutive sold-out shows between Dec. 16 and 20. (Rachael D'Amore)

Freudian may be his first full-length release but previous EPs Birds of Paradise, Praise Break and Pilgrim’s Paradise follow closely behind. Each effort is built on the same pillars of lovelorn lyrics stirred with smooth, soulful harmonies but Freudian, Caesar says, is more an “introspective piece” that delves into the complex “relationships with women” in his life.

“It’s Freud’s teachings,” he says. “Your parents are your example for love and however that dynamic works, you’re going to carry it throughout your life. This is me trying to figure that out. Through figuring that out, you figure yourself out, and through figuring yourself out, you feel like you’re closer to happiness... Happiness is the bottom line.”

But is Daniel Caesar happy?

“From time to time,” he says with a laugh.

Caesar is honest about the low points he’s endured throughout his life so far. As the son of devout Christians, he says he “grew up in a bubble” and struggled to cope with the very little freedom he was given.

His father, Norwill Simmonds, is an accomplished gospel singer who used to preach to him about “negative experiences” he had while involved in the music industry. While Caesar acknowledges the influence his parents ultimately had on his music, he says his dad was constantly deterring him from getting into the business.

Eventually, after getting kicked out of his Christian private school in Oshawa, he fled to Toronto to find the freedom he longed for.

But things didn’t go so smoothly.

“I had this job but I was crashing on people’s couches. I would try not to stay in one place every night so not to bog anyone down but some nights I wasn’t proactive enough during the day and didn’t figure out where I would stay at night so when I got off work, I’d knock on friend’s doors but no one was up,” he said.

“I’d sleep in Trinity Bellwoods… I’d sleep on benches, McDonald’s, at Dunbat skate park. I just walked around there all night one night. It was kind of crazy.”

Daniel Caesar
The bench in Toronto's Trinity Bellwoods Park where Daniel Caesar says he spent several nights while homeless after making the move from his home in Oshawa to Toronto. (Rachael D'Amore)

While lying on a bench near the corner of Ossington and Dundas one night, Caesar had a bit of an epiphany.

“I bought these $300 shoes knowing that I couldn’t afford them and the next week I was sleeping on the bench, using my backpack as a pillow, wearing these expensive shoes that I had no business owning,” he said.

“I was on the bench looking at my feet shaking my head thinking, ‘How did I get myself here? What am I doing?’… There were dark days but no one could tell me what to do. It was fun, but I learned the hard way."

"It was part of the process, not part of the plan, but a very important part of the process.”

After finding mentorship in Ajax rapper and producer Sean Leon and his artist collective IXXI, he started to find his groove.

Flash forward a couple years, four music videos and more than 50 million streams on Apple Music of his major hit ‘Get You’ later, Caesar has made something from nothing.

Daniel Caesar
The basement of The East Room where Daniel Caesar shot the music video for his major hit 'Get You.' (Rachael D'Amore)

Now, he can sit on the same bench in Trinity Bellwoods Park that once acted as his mattress and feel at peace with his disordered journey. Back in 2016, Caesar brought his past into the present with an acoustic performance in that very same park on that very same bench, fittingly titled Trinity Bellwoods Sessions. There, on a summer day, Caesar played to dozens of parkgoers and fans who sat in the grass and listened to him perform a mixed bag of originals and covers.

“It was awesome to come back to that spot because finally I wasn’t looking at the end, I was looking ahead. That was my rock bottom but to come back there and have over 100 people sit at my feet and listen, it was really special,” he said.

“I knew I wouldn’t be doing that forever, sleeping outside. That wasn’t part of the plan.”

Since then Caesar has glided down a waterfall of success. Despite achievements and international accolades, he’s stayed faithful to the small, DIY music label helmed by his some of his closest friends, Golden Child Recordings. While other offers have trickled in, Caesar says he’s deflected them, not only as a “business move” but to “set an example and send a message.”

“One thing my dad would always preach to me, he would always talk to me about the dangers of signing away the things you own to other people,” he said.

“If you can make it work without it, if you can build a house without going to the bank for a loan, then do that.”

While there’s clearly room (and desire) for Caesar to take the bait being dangled from the across border, he’s frank about wanting to keep his success home grown.

“No, no, no,” he says with a snarl. He shakes his head a few times before laughing.

“Shout out to America, but I’m good over here. I love Toronto. It’s my favourite place on earth.”

With files from CTV News Toronto's Tracy Tong