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.

Woodbine was featured as a regular on the NBC midseason sitcom Battery Park and played Dr. Damon Bradley, who later turned out to be a serial rapist,[5] in the short-lived CBS medical drama City of Angels, the latter of which earned him a nomination for the NAACP Image Award for Outstanding Supporting Actor in a Drama Series.

In 2009, Woodbine appeared in the blaxploitation film Black Dynamite[3] and followed it up the next year with the M. Night Shyamalan-produced supernatural thriller Devil.

He played Daryn Dupree, who was part of a police task force that investigated the murders of rappers Notorious BIG and Tupac Shakur.