Entering the new millennium, 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, 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. Additionally, he appeared in the Wu-Tang Clan's music videos for their songs "Protect Ya Neck II (The Jump Off)", "Gravel Pit", and "Careful (Click, Click)". Woodbine went to portray saxophonist David "Fathead" Newman in the Oscar-winning Ray Charles biopic "Ray".