Throughout his childhood, James would sing regularly, but never in public. He eventually moved to New York where he was influenced by his aunt Rosie Gaines, a former singer for Prince. His love for the album Purple Rain landed him in a studio at the age of 19. His skills as a songwriter began with the song "Portrait", leading up to a credit on the single "Use Me" by R&B singer Miguel after forming a bond with him on MySpace.
James performed in and around New York with artists such as Luke James and Wynter Gordon. In 2013 he released his first EP, a three-part entitled Coke, Jack and Cadillacs. Each part represented important themes in his life - first love, first drink, first car. The EP featured songs that included "A.D.I.D.A.S." and "Pledge Allegiance". It also featured Asher Roth on the song "Lisa". James signed with ByStorm Entertainment/RCA Records in 2015 and subsequently released "Permission", his first single from a major record label, reaching number 37 on the US Hot R&B/Hip-Hop Songs chart. His debut album, Eldorado was released May 27, 2016. It debuted at number 71 on the US Billboard 200 and at number eight on the US Top R&B/Hip-Hop Albums. It subsequently earned him his first nomination for Best R&B Performance at the 59th Grammy Awards in February 2017.