Steeples began studying acting at the St. Louis Repertory Theatre. By the mid-90s Steeples had moved to New York City where he joined an avante-garde hip hop group, No Surrender, as well as an experimental movie outfit called Mo-Freek helmed by director Kevin Ford. Throughout the ensuing years, Steeples' versatility as an actor allowed him to play a number of leading roles. He flexed his comedic skills as the Rubberband Man in the Office Max commercials and on the groundbreaking The Chris Rock Show. He also played a dramatic lead in the award-winning short film Whoa, which premiered at the Sundance Film Festival.

Steeples can be seen in Akeelah and the Bee, with Laurence Fishburne and Angela Bassett, and has also played leading roles in several of Kevin Ford's independent features such as Caravan Summer, People Are Dead (co-starring Angela Bettis, Mia Tyler, and Cinque Lee) and Lost in The Bush (co-starring Brent Roam). Another project he appeared in was the political documentary Amadou, inspired by the Amadou Diallo police protests that swept Manhattan in 1999.

While in New York, Steeples also got behind the camera shooting for various Mo-Freek productions, as well as serving as a cameraman for the show Street Team TV, where he filmed artists such as Jermaine Dupri, the Ataris and Nas. Since relocating to Hollywood, Steeples has received considerable attention for his role of Rasan in the action movie Torque with Ice Cube, Faizon Love and Jaime Pressly (his Earl co-star). In 2004 Steeples co-wrote a film, Robbers, which he also acted in and co-directed with Chris Sivertson.