Ryan Montgomery, born and raised on the West Side of Detroit, Michigan in the W. McNichols & Wyoming Ave. area, moved to Oak Park, Michigan when he was 10 years old, later acquiring the nickname "Royce" during highschool after wearing a Turkish link chain with an R pendant resembling the Rolls Royce symbol. He began rapping at 18, influenced mainly by Ras Kass and Redman; he signed his first deal in 1998 with Tommy Boy Records, recording an album for them called Rock City, referring to Detroit's former status as home to Motown Records. When the project was heavily bootlegged, Royce left the label for Koch to re-record some of the album, eventually releasing it in 2002 as Rock City (Version 2.0). While the album didn't sell very well, the DJ Premier-produced single "Boom" gained 5'9" some underground recognition and eventually resulted in the two working together more closely.

Through his manager, Royce was introduced to Eminem at a show in 1997, and the two formed a working relationship; they formed up as a duo, Bad Meets Evil, and released several tracks together, including one called "Renegades", from which Royce's vocals would later be replaced with Jay-Z's on the latter's The Blueprint. Through Eminem, Royce would also be introduced to both Dr. Dre and execs at Game Recordings. After his manager revealed that Royce was involved in writing the tracks "The Message" and an original version of "Xxplosive" for Dre's 2001 (entitled "Way I Be Pimping"), Dre requested that Royce cut ties with his manager. Royce refused to fire his manager and his relationship with Dre ended.