Woodward is one of the few actors to have crossed over onto three series created by Joss Whedon: Buffy the Vampire Slayer, Angel, and Firefly. He appeared as Holden Webster in the Buffy the Vampire Slayer episode "Conversations with Dead People", as Knox in the fourth and fifth seasons of the series Angel, and as Tracey in the Firefly episode "The Message". All three characters appear friendly or helpful when first introduced, but each is eventually killed by the series' protagonists when revealed to be more sinister. In addition, all three characters appear in connection with a grave or coffin of some sort. In 2010 he starred in the film Drones directed by Buffy alums Amber Benson and Adam Busch.