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Obadiah Stane was a ruthless individual who studied his adversaries to find weaknesses that he could exploit them. As a child, Obadiah lived in poverty while his father was a degenerate gambler (and possibly a drunk). One day (sometime after his mother died of unknown reasons), Obadiah saw his father on a "lucky streak"; played a game of Russian roulette and (accidentally) shoot himself in the head. The psychological trauma caused Obadiah to lose all of his blond hair and go bald and shaped him for years to come. From there on, Obadiah Stane was a ruthless manipulator who studies his adversaries to find weaknesses to exploit. Stane enjoys chess, and lives his life with the same kind of methodical logic that he uses in the game. In addition, he is a strong believer in using psychological manipulation to his advantage. For instance, in a childhood chess match against another boy whose skill at least equaled his own, he killed the boy's dog so that the other would be distracted from the game.
In adulthood, as a wealthy financier, Obadiah Stane turned his sights on acquiring Stark Enterprises, the industrial corporation when it was originally owned by Howard Stark, but failed. Stane tried again when it was currently owned by Tony Stark (a.k.a. Iron Man). Stane had his agents, the Chessmen, attack Stark International and assault Stark's confidante, James Rhodes. Stane also set up Indries Moomji as Stark's lover without Stark knowing that Moomji was actually the Chessmen's Queen. While all of this was occurring, Stane and his associates conspired to lock Stark International out of various business deals. Stark eventually learned that Stane was the mastermind behind these attacks, but was unable to confront him. The assaults on Stark, his business, and his friend pushed him to the edge, and when Stark was scorned by Stane and then spurned by Moomji, he catastrophically relapsed into alcoholism. With the help of S.H.I.E.L.D., Stane succeeded in buying out Stark International, which he then renamed to Stane International. Stark, having fallen off the wagon, relinquished his armor to Rhodes and disappeared to be a homeless vagrant. Rhodes became the new Iron Man while ignoring Stane's demands to relinquish the armor.
Stane proceeded in manufacturing and supplying munitions and weapons to S.H.I.E.L.D. and others who could pay for them. But, when Tony Stark left, he left behind notes and information on the Iron Man armor. These notes were far from complete and without Stark's mind, they were hard to analyze, but Stane assigned a team of scientists to these notes and working from this, they created the Iron Monger Armor, which, according to Stane, was "far superior to Stark's Iron Man armor". He even thought of either selling them to the highest bidder or creating an army of them and using them to "take over any country he wanted". He said that this last idea was particularly interesting.
Stark, while a vagrant, befriended a pregnant homeless woman. She died in childbirth, but Stark promised to protect the child. This vow helped pull Stark out of his alcoholic state. When Stark recovered, he built a new suit of Iron Man armor, creating what was then the pinnacle of armor design, the Silver Centurion armor; he also founded a new, successful computer company, Circuits Maximus. Upon learning of his rival's recovery, Stane decided to attack Stark continually again. Stark confronted Stane on the property of Stane International and defeated Stane's agents, including the Chessmen, who had proven a match for his previous armor. Stane donned the Iron Monger armor and confronted Stark personally. The Iron Monger was more powerful than the previous Iron Man armor, but not the Silver Centurion model. Stane tried to defeat Stark by threatening to give his friends a horrible death, but Stark easily defeated the deathtraps. He then confronted Stane again, who was holding his last card: the baby of the woman who Stark had befriended while on skid row. Stane told Stark to remove his helmet or he would crush the homeless woman's baby between his palms. Stark, having detected interfering frequencies in his armor's systems through the battle, deduced that Stane wasn't experienced enough to pilot the armor without some help in the form of an external computer. He used his armor's pulse bolts to destroy the nearby building that contained that computer, causing Stane's Iron Monger armor to seize up and fall to the ground as Stark swooped in to catch the baby. Stane then removed his helmet and confronted Stark. When Stark told Stane that it was all over, Stane said that he had one thing left. He then raised his hand to the side of his head and using the Repulsor beam, he fatally shot himself in the head, like his father before him.
Iron Man: Armored Adventures
For the full page on the animated character see here
Marvel Cinematic Universe
(For the main page on the Marvel Cinematic Universe version see here