19 on the '20 Best R&B Albums of 2014' by Rolling Stone. In 2014, Caesar received widespread critical acclaim for his debut EP Praise Break, which was ranked No. The turning point of Caesar's career came in 2015, with the release of his second EP, Pilgrim's Paradise. After leaving his home, he began doing gigs.

He felt no choice but to pursue his calling as a musician. At the age of 17, Caesar was kicked out of the house after a fight with his father on the weekend of his high school graduation.

Caesar longed for the city, which was an hour’s drive from his home. He was raised listening to soul and gospel delivered though musicality and religion, even though his parents were cautious of temptations that came with music. Ĭaesar grew up in church, singing before his father's congregation in Oshawa. Caesar attended the Seventh-day Adventist Church and private school in Oshawa. He is the second eldest of four children to his mother Hollace and father Norwill Simmonds, a pastor and gospel singer who released his first album as a high school student in Jamaica.