Leeroy's rap career took off when he began performing "Leeroy" in clubs, for which he would don blackface and act like a stereotypical nigger. Moon Man invited his cousin to record the song for his King Nigger Killer EP, for which Leeroy would also record "Moon Gates" in an imitation of Moon Man. Leeroy would return to work with Moon Man for the New Era EP, for which he recorded "Hotline Leeroy", this time without the blackface.
In spring of 2016, Moon Man and Leeroy recorded a whole EP together, called Moonman and Leeroy.
It has been postulated that Leeroy is actually nothing more than a voice in Moon Man's head.