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After Howard Stark rejects Stane's plans to weaponize the Earth Mover project, he is believed to have caused the aircraft that the Stark's were on to explode, killing Howard Stark, but leaving Tony a survivor, and continues to deny any involvement in the crash. After this, Obadiah becomes the new Acting CEO of Stark International, as Tony is too young to assume the post, and ignores the boy's request to be involved.
When Tony Stark first becomes Iron Man, Obadiah immediately becomes interested in his armor, and tries to get Iron Man to join him. In Iron, Forged in Fire Part 2, Obadiah tests out the new weaponized Earth Movers against Iron Man only for the Mandarin to attack and target one of the Makluan Rings that Obadiah is wearing. Obadiah quickly surrenders the ring to the Mandarin. After a brief fight between the Mandarin and Iron Man, Obadiah tries one last time to get Iron Man to join him, in vain.
In Cold War, it is revealed that Stane was responsible for the disfiguration of Donnie Gill, the scientist who became Blizzard. In an attempt to create a new weapon, Blizzard and Iron Man make and alliance against him, but Iron Man (understanding that Blizzard has no consideration in killing innocent people to get Stane) eventually turns against him and reluctantly saves Stane from the freezing villain. Instead of thanking him, Obadiah expresses his disappointment that Iron Man is still alive, and vows to take the armor from him. Losing patience with his threats, Iron Man just answers "Your time is coming. Stane", before shooting his camera.
In Field Trip, it is revealed that Stane has a daughter named Whitney Stane. He has no serious interest in his daughter, except for her homework and she apparently dislikes him. This later causes her to become Madame Masque and impersonate him and then frame Iron Man.
In Seeing Red, he makes a deal with Project Pegasus scientist Anton Harchov to sponsor the research that anton is working on. Obadiah has the Crimson Dynamo upgraded before sending it with O'Brian (Stane's head of security) to get Iron Man. Though the Crimson Dynamo succeeds in capturing the hero, Iron Man is able to escape before they open the armor thanks to a diversion caused by Pepper. After the Crimson Dynamo is defeated by Iron Man in his own Dynamo armor and the Technovore virus eliminates the data on the Iron Man armor and the Crimson Dynamo armor, Obadiah tells his secretary to tell Anton that his offer is rescinded.
In Best Served Cold, Madame Masque makes one of her attempts on her father's life which is when Obadiah learns of her true identity upon being subdued. When Whitney falls ill from the effects of her mask, Obadiah calls in Tony to tell him about the mask. In order to obtain a cure for Whitney, Tony takes the Arctic armor to an abandoned arctic base where an unrefined ore is located to help cure Whitney. Obadiah thaws out Blizzard and places an explosive on his costume in order to get him to obtain the ore first. When Blizzard goes back on the deal and freezes the explosive, he attacks Obadiah only to end up fighting Iron Man and Madame Masque. After Blizzard is defeated, Iron Man knocks out Obadiah so that Madame Masque couldn't kill him. After Whitney is cured, Obadiah thanks Tony for curing his daughter.
In the two-part episode Tales of Suspense, the Mandarin admits he's the one who caused the plane crash, thus revealing to Tony, his friends and the viewers that Obadiah Stane is really innocent.
In the two-part season premiere, Obadiah Stane is kidnapped by Whiplash at the request of his employer, Justin Hammer, who wants him out of the picture, permanently. Stane makes one attempt to escape but is stopped by his old enemy, Blizzard who was hired by Mr. Fix to guard him. Iron Man and War Machine rescue him for the second time, and Stane remarks that it doesn't change anything, and that he will own his armor. They get him out of captivity, but not before leaving him on an empty building rooftop as a joke.
The Stark International board is losing faith in Stane who want the Iron Man suit that he keeps saying that he'll get. Eventually, Stane hires the Ghost to get his armor specifications one way or another. The Ghost had succeeded in getting the specs and Obadiah finally got what he wanted for a long time, the specs for the Iron Man suit.
Obadiah Stane uses the plans he acquired from Ghost to build the Guardsmen armors. He also makes a public service announcement about his Guardsmen making plans to bring down Iron Man and announces the Guardsmen Expo coming up. When the day comes for the Stark International Guardsmen Expo, Obadiah Stane introduces Firepower as the third Guardsmen when Iron Man appears. Using the hacking of the televised screen at the expo, Iron Man reveals that the identities of Force and Shockwave were actually criminals much to the surprise of Stane. Obadiah Stane later makes a televised appearance stating that he had no idea the criminals used fake identities in order to get jobs at Stark International. Obadiah Stane later prepares to complete Project Monger as the field test for the Guardsmen is complete.
Stane aligned himself with Doctor Doom to perfect the power core for Project Monger, in exchange for the Iron Man specs. Doom reduced its size and increased its power in only three hours, but Doom has rigged it so it would explode, destroying the entire city. But that outcome was prevented thanks to Iron Man.
When Stane finally perfects the Iron Monger mech, the Stark International board aren't impressed because it isn't Stark tech. Obadiah offers Tony to be back in Stark International. He refuses, but changes his mind later. He finds out about Stane's Iron Monger and witnesses its abilities as it demolishes a condemned building. Tony sees an old man running into the building. He runs off and changes into Iron Man. Obadiah orders O'Brian to continue decimating the building, but stops once he sees Iron Man and the old man. Tony later criticizes Stane for willing to risk lives. Later, Stane pilots the Iron Monger himself to continue demolishing the building with the old man still inside, passing him off as collateral damage. Iron Man and War Machine fight the Iron Monger and can't even damage it. Iron Man discovers that Stane needs external computer help to operate the Iron Monger. At Iron Man's request, he takes a radio jamming device and short circuits the Iron Monger, defeating Stane. He was later forced to renouce ownership of the building to the old man in exchange for him not suing Stark International.
Tony's patience on Stane has reached its limit, he decides to put an end to this conflict. Rhodey tries to cheer Tony up, he realizes that he has a video of Stane about Stane and Ghost's deal over the Iron Man specs, which could be used as evidence. Tony tells Rhodey's mother about this and they both show the board the holographic tape just after Stane becomes permanent CEO. The board, enraged by this video, fires Stane and Tony gloats at his failure. Stane immediately realizes that Tony is Iron Man and decides to go on a rampage using Iron Monger and attempts to attack everyone he cares about until Whitney prevents him from doing any further. Justin takes this as his advantage to get the military contract due to taking "heroic" actions and orders Sasha to take control of Iron Monger while he attacks it. Titanium Man attacks Iron Monger and eventually Stane falls off of a building. He is badly injured but the Iron Monger took most of the fall's damage. Tony and Whitney visit Stane in the hospital but Whitney blames Tony for the event.
Obadiah Stane's body was taken by Whitney Stane and put in a secluded place in bed, but was discovered and put back into the hospital.
Obadiah Stane is a ruthless and cold-hearted individual who is primarily interested by money. He uses his company to build and sell weapons to make a higher profit without considering the deaths that they would cause (contrary to Howard Stark, the former CEO). He's obsessed in acquiring Iron Man's armors in order to mass produce them for commercial gain.
However, as he has shown several times, he is less cruel than he seems and can at times be a decent man. He deeply cares for his daughter Whitney, he once called the FBI to warn them about the attempted assassination on Tony Stark, and when he sent Crimson Dynamo to capture Iron Man, he scolded his associate for putting thousands of innocent lives at risk while doing it, saying that "I may make weapons, but I'm no murderer!". During his final battle against Iron Man, his daughter Whitney manages to reason him and he really seems to regret what he did, unfortunately Titanium Man takes control of Iron Monger control and makes him continue his rampage.