4. Madame Masque
Madame Masque was once Whitney Frost, a wealthy socialite who became one of Tony's many girlfriends. When Whitney discovered her father was the supervillian Count Nefaria, she willingly accepted her place as leader of the Maggia, a Mafia-like organization running the East Coast of the US. Her role as Maggia leader brought her into conflict with Iron Man. Whitney was forced to flee after a raid on his company, Stark Industries. The plane she escaped in crashed and Whitney's face was scarred, but she was saved by the criminal Mordecai Midas and started to work for him as his agent. Midas was obsessed with gold and Whitney hid her face behind a golden mask and used the alias "Madame Masque" Madame Masque met Tony Stark and he showed concern for her despite her scarred face. She turned on Midas to save Stark, but left Stark because of her criminal past. Unable to forget him, she returned as Krissy Longfellow, Stark's personal secretary. Both came to know each other's secret identity and started a romantic relationship. After her father was left fighting for his life, she brought him to Stark to find a cure, But a fight broke out between her Father and Tony. During the battle Whitney was unable to choose between her father and her lover and when Nefaria's life-support was damaged in the fight, she went insane with guilt and grief. Whitney Frost is the Catwoman to Tony Starks Batman.