Machine Man limited series (1984)
Chronologically, Iron Man's apparent first adventure took place in 2015 when the terrorist Robert Saunders managed to arm a nuclear device in one of Stark's massive industrial plants. Arno Stark had just finished work on a "time displacement device" and thus used it to travel back to the year 1986 to obtain the retina patterns of the now-dead Saunders. On the verge of success, an inquisitive Spider-Man thwarted Arno's efforts, and after nearly being beaten by Spider-Man in battle, Arno was suddenly whisked back to the future, ahead of schedule. The bomb Saunders had armed detonated prematurely, thus destroying not only the time machine, but also killing Stark's wife and child (not to mention a good portion of the surrounding area).
In 2020, robotics corporate giant Sunset Bain enlisted Iron Man's assistance in stopping a group of Midnight Wreckers who had accidentally stumbled upon the disassembled body of Machine Man. The Wreckers managed to put Machine Man back together and with the Wreckers came into battle with Iron Man. Machine Man soundly defeated Arno, so much so that Arno began to re-evaluate his role as an armored hero. Nevertheless, business rival Wellington Marcus called upon Stark to find his missing daughter who had been recently kidnapped and held for ransom. Stark agreed, but discovered that Marcus was secretly behind a plot to sabotage the world's computer systems. Iron Man fought Marcus (who had built his own suit of armor) and defeated him. After this victory it is revealed that Tony Stark is actually one of Arno's closest confidantes.The victory over Marcus was a rare event for Iron Man as his character has vacillated between the role of hero and villain throughout his career. Aside from his defeat against Machine Man and his victory over Marcus, Iron Man was once summoned by Immortus to battle the Avengers as a member of the Legion of the Unliving, seemingly placing him in the villain camp again. His subsequent tussles with Death's Head and Spider-Man and Cable only served to further blur the actual role of Arno Stark. Further, he was one of Machine Man (X-51)'s Heralds but was later witnessed in a temporal jail. These also serve to muddle the exact position Iron Man.