He is the second eldest of four children to his mother Hollace Burnett-Simmonds and father Norwill Simmonds, a pastor and gospel singer who released his first album as a high school student in Jamaica.

[9] 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; he was briefly homeless during this time.

He connected with producers and future collaborators Jordan Evans and Matthew Burnett and began writing and recording what would be his debut EP Praise Break in 2014;[10] it was No.

[9] The album received positive critical acclaim and, while not immediately a commercial success, tracks like "Streetcar", the cover of Kanye West's 2008 song "Street Lights", have become fan favorites.

The album featured guest appearances from Brandy, Pharrell Williams, John Mayer, Sean Leon and Jacob Collier.

His music draws from his childhood experiences and integrates them with R&B and electronics, while his lyrics explore subjects of religion, philosophy and unrequited love.

"[9] Caesar cites Frank Ocean, Kanye West, Beyoncé, and The Doors frontman Jim Morrison as musical and stylistic inspirations.

[9] Caesar works in close collaboration with producers Matthew Burnett and Jordan Evans, with whom he co-founded his independent label, Golden Child Recordings, and has co-produced almost all of his music with since 2015.

[24] Caesar is also part of an informal collaborative of Toronto-based musicians and songwriters that includes River Tiber, BadBadNotGood, and Charlotte Day Wilson, among others.