Jimmy Lee is one half of the titular duo from the Double Dragon video game series. While Jimmy is traditionally portrayed as a protagonist for most of the series, fighting evil alongside his twin brother Billy, he's also been portrayed as an antagonist in two notable works.
Double Dragon (NES)
In the NES version of the original Double Dragon, Jimmy Lee is the secret leader of the Black Warriors gang. Whereas the original arcade version had both Lee brothers working together to fight against the Black Warriors in order to rescue their female friend Marian, in the NES version Billy fights completely alone and Jimmy only shows up to confront him after Willy Mackey (the leader of the gang in the arcade version) is defeated by the player.
Presumably this change in the story was done due to developer Technos Japan's inexperience with the NES hardware at the time, making it difficult for them to work around the console's limitations and properly implement a 2-player cooperative mode in the game's conversion. The title wouldn't had made much sense with just one of the Lee brothers in the game, so they made the other one into a bad guy. While the arcade version did feature a fight between both brothers, it was an optional battle that occurs if both players defeat Willy together and was simply a contest over who wins Marian's affections. The game's sequels on the same platform, Double Dragon II and III, both included their own 2-player co-op modes, thus having both Lee brothers as heroes again. Jimmy's change of status from an antagonist to a protagonist in the NES versions of the sequels was left unexplained.
Double Dragon (cartoon)
The Double Dragon animated series loosely adapts the plot of the NES version for its first two episodes, having Jimmy as the show's initial antagonist. Prior to the events of the first episode, the Lee brothers were separated at birth after Jimmy was kidnapped by their half-uncle, the Shadow Master, who raised him and trained him in the way of the Black Flame, while Billy was raised by their father's sensei, the Eldest Dragon. When the twins reached the age of 18, Billy inherits the title of Dragon Master, becoming wielder of the legendary Dragon Sword, while Jimmy is already active as the Shadow Boss, the Shadow Master's second-in-command and wielder of the Shadow Sword. Billy eventually learns the truth about Jimmy and tries to convince his brother to change his ways. When the Shadow Master betrays Jimmy by ordering his assassination due to his failure to recover the Dragon Sword, Jimmy abandons his evil ways and join forces with Billy as the Double Dragons, fighting against the forces of the Shadow Warriors for the remainder of the series. His Shadow Sword also becomes a second Dragon Sword in the process.
- The handheld LCD game and board game versions of Double Dragon produced by Tiger Electronics both referenced Jimmy Lee as an antagonist rather than going by the arcade version's storyline.
- The instruction manual for the Game Boy version of Double Dragon copies the plot blurb from the NES version and refers to Jimmy as the Shadow Boss. Despite this, Jimmy never actually shows up in the single player mode, as the game ends after the player defeats Willy like in the arcade version.
- The manual for the Genesis version incorrectly identifies Machine Gun Willy as Jimmy, due to the author mixing up the differing storylines of the arcade and NES versions, despite Willy looking nothing like the Lee brothers.