The Shadow Boss may refer to:
- Jimmy Lee's title in the NES version of the first Double Dragon, where he is the secret leader of the Black Warriors. In the Double Dragon animated series, the Shadow Boss was the name of Jimmy's alter-ego when he was in the service of the Shadow Master.
- Willy Mackey, who is referred to by the title of Shadow Boss in some versions of the original Double Dragon, particularly the Atari 2600/7800 versions.
- The Shadow Boss from Battletoads & Double Dragon: The Ultimate Team, who is a loose amalgamation of various characters from the original games.