Sir, Have you ever thought of renouncing your playboy life -- your wastral ways-- and joining S.H.I.E.L.D.? 
Appearing in "If Bucky Lives...!"
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- The Earth-Digger
- Iron Man Armor Model 3
- A Mechanical Dragon (First appearance)
Synopsis for "If Bucky Lives...!"
The Mole Man has used a device to cause Stark Industries factory to fall into the ground so that he may capture the atomic powered earth borer which Tony Stark was developing. As Iron Man, Stark attempted to stop the Mole Man who triggered a cave in.
Iron Man survives the cave in to find that Pepper Potts was also in the factory (even though Stark had told her to leave when he was testing the device), they are both attacked by the Mole Man's Moloids. After the Mole Man explains his intentions, Iron Man is able to fight off the Moloids and fly Pepper to safety. There he contacts the US Military to explains what is going on but cautions them to allow him to do things on his own first.
The Mole Man counter attacks, unleashing a creature which is akin to a fire breathing dragon. While Iron Man fights off this beast, the Mole Man kidnaps Pepper and takes her back to the boring device. Iron Man defeats the monster and catches up to them. The Mole Man orders Iron Man to show him how the boring device works in exchange for Peppers life. Iron Man instead instructs the Mole Man how to cause the device to overload with radiation and explode, escaping with Pepper just before it does so, seemingly killing the Mole Man in the process.
Appearing in "If A Man Be Stone!"
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Synopsis for "If A Man Be Stone!"
Tony Stark has returned to his factory for the first time since he came back from Vietnam to find the place under full alert because somebody had broken in. Taking a group of security guards, they burst in to find that the intruder is S.H.I.E.L.D. agent Jasper Sitwell, who has been assigned to protect Stark Industries during Stark and Iron Man's leaves of absence.
Meanwhile, the Grey Gargoyle has escaped from prison, and seeks cover in his civilian guise of Paul Duval. He reads in the paper about Stark Industries development of a cobalt super-weapon, which he hopes to steal in order to use to obtain Thor's Hammer, which the Gargoyle believes will grant him immortality.
Resuming his guise as the Gargoyle, he attacks Stark Industries turning any who get in his way into stone. Stark manages to get away from Jasper long enough to change into Iron Man and tries to confront the attacker. Jasper gets in the way and has his weapons turned into stone for his troubles. Iron Man continues to fight the Grey Gargoyle, but eventually the Gargoyle begins slowly changing him to stone. While Jasper tries to call S.H.I.E.L.D. for back-up (his radio he finds is broken) the Gargoyle succeeds in turning Iron Man into stone and throws him off the Stark Industries building... This story is continued next issue...