With the encouragement of his actress mother, Woodbine entered show business at age 19 as a stand-in and extra in Ernest Dickerson's directorial debut, "Juice" (1992), starring Tupac Shakur and Omar Epps. In the following year, he made his TV acting debut in the "CBS Schoolbreak Special" entitled "Love Off Limits". His appearance was noticed by casting director Jaki Brown-Karman, who later recommended him to Forest Whitaker for the latter's directorial effort, the HBO television movie "Strapped" (1993). Since then, he has worked with other major African-American filmmakers such as Spike Lee, Mario Van Peebles and the Hughes Brothers in the films "Crooklyn" (1994), "Panther" (1995) and "Dead Presidents" (1995), respectively.