Jermaine Crawford's first and most well-known role was as Duquan "Dukie" Weems in HBO's crime drama series "The Wire." At the beginning of the show's fourth season, Weems shows promise as a student but eventually succumbs to the drug-addled environment of his Baltimore neighborhood, becoming an addict himself. Crawford's background in musical theater as a child likely played a large part in his role as Darren in the play and film versions of the musical drama "A Mother's Prayer," starring Robin Givens and Johnny Gill, about a religious African American family dealing with the impending death of a matriarch.
The same year, Crawford had a bit part in the independent film "An American Affair," which focused on a teen obsessed with a neighbor (Gretchen Mol) who becomes entangled in a scandal with John F. Kennedy. The following year, Crawford took a slightly larger role in another independent film, the teen-centered thriller "Twelve." Similar to his role in "The Wire," Crawford played an at-risk inner-city youth involved with drugs and violence.