Park benches in Toronto, then the Grammys

Daniel Caesar grew up in Oshawa, Ontario. According to a December 2017 CTV News Toronto profile, he was asked to leave his private school there, and he moved to Toronto in search of the freedom he felt he had been denied. He was in his early twenties when he made the move, and he had a job, but he had no settled place to live.

For a time he couch-surfed and often did not plan where he would sleep. He spent nights on benches, at a McDonald's and at the Dunbat skate park, and he slept in Trinity Bellwoods Park. A photo caption in the article refers to several nights spent homeless. One night he simply walked around the area until morning. The article does not give a set duration or a precise year, saying only that it happened a few years before it was written.

A turning point came as he lay on a bench near Ossington and Dundas. He realised he had bought 300 dollar shoes that he could not afford, and that he was now sleeping on a bench while wearing them. He said he learned the hard way. Looking back, he described the time as part of the process, not part of the plan, but a very important part of it.

His circumstances changed when he found mentorship in Ajax with the rapper and producer Sean Leon and his collective, IXXI, and he began to find his footing. His debut album, Freudian, earned two Grammy nominations. He sold out five shows at the Danforth Music Hall, and the song Get You passed 50 million Apple Music streams. He continued working with the independent label Golden Child Recordings and became one of Canada's leading R&B artists.