- Obadiah Stane
- Madame Masque (Whitney Stane) (First appearance as Madame Masque)
- Mister Fix (Mentioned)
- Maggia (Mentioned)
- A.I.M. (Advanced Idea Mechanics) (Mentioned)
When Obadiah starts acting strangely, Iron Man investigates and discovers that "Obadiah" is being impersonated by a villain named Madame Masque. Madame Masque causes him trouble by destroying his art gallery and his private garage at the pier. When Iron Man discovers her (though both are unaware of each other's identity) and threatens to call the police, she copies her appearance and impersonates him as a thief, causing him to be wanted by the police. After her father ignored her, again, Whitney decided that if making him losing the things that he loves doesn't free up some time with her, then she'll get rid of everything else, including Iron Man.
Madame Masque fights Iron Man at the train yards, however; when she attempted to kill him, she accidentally changed faces in front of the police, forcing her to run. She barely catches on to the ledge of a building and as Iron Man approached her, her mask fell off, revealing her face as the daughter of Obadiah Stane. Not wanting his friend to go to jail, Tony/Iron Man let her off with a warning.