Despite being a billionaire playboy super-scientist, Tony Stark hasn't exactly had an easy life. Nevermind the trouble he's faced as Iron Man fighting bad guys, just being Tony Stark has caused him issues. Unlike the real world, in the Marvel Universe being a billionaire doesn't insulate a person from most of their problems. But it's not all bad. Along the way he's made some great friends, and even saved the world a few times.

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For this list, we're looking at ten of the most important moments in the Armored Avenger's life, talking about how they came about, and how they've affected him.

10 ORIGIN

original Iron Man

Like every superhero, Iron Man has a classic origin story. For Tony Stark, it began after he was attacked by enemy forces during the Vietnam War...or guerilla forces in Southeast Asia...or during the Afghanistan war. The era has been re-written numerous times, but the end result is always the same: Tony Stark builds a suit of armor (in a cave...with a box of scraps) that allows both for him to escape, and for his heart to keep beating after it was embedded with shrapnel. Realizing he had a good thing going, Stark decided to use Iron Man as his bodyguard.

9 STRUGGLE WITH ALCOHOLISM

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One of Tony Stark’s longest running issues has been his struggle as an alcoholic. At this point, it’s the flaw that remains regardless of how the character changes, gets rebooted or reset. It all began during the 1979 classic story “Demon in a Bottle”, by David Michelinie and Boby Layton. After being manipulated and having his armor hacked by his business rival Justin Hammer, Stark begins to turn a bit more heavily to drinking to deal with his issues. Despite eventually dealing with Hammer, his drinking problem remains until his then-girlfriend, Bethany Cabe, points out his problem. With her help, he’s able to give up drinking, but it remains an issue that haunts him to this day.

8 MEETING RHODEY

David Michelinie wasn’t just responsible for some of the best stories of Tony Stark’s career, he’s also responsible for introducing one of the most important people in Tony’s life that isn’t a love interest: James “Rhodey” Rhodes.

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Though the character starts out as just a simple helicopter pilot when he’s first introduced, Rhodey would go on to become one of Stark’s best friends and closest confidants. That hasn’t always been the case though, as Stark’s habit of being secretive and making unilateral decisions that affect others has occasionally caused some huge rifts between them. It didn’t stop Stark from granting Rhodey the War Machine armor, though.

7 LOSING HIS COMPANY

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Stark’s got a litany of rogues aiming to take him out just like anyone else, but the ones who do the most damage tend to have resources and power just like him. After years of coping with his alcohol addiction, Stark fell off the wagon during his encounter with his business rival Obadiah Stane. Stane attacked Stark from all sides, breaking him down until he had successfully stolen his company. This eventually drove Stark to drinking again, and when he fell off the wagon he fell off hard, eventually winding up homeless. A story from the great Denny O’Neil, Stark’s struggle to reclaim everything he lost took nearly 40 issues to complete.

6 ARMOR WARS

Shortly after David Michelinie’s return to the Iron Man ongoing, he started what’s probably the second most well-known storyline after “Demon in the Bottle” in “Armor Wars”. When designs for his weapons and armor are stolen by Spymaster, Stark goes on a one-man mission to take out every person using weapons based on his designs. He tears through heroes and villains alike, narrowly avoiding international incidents but ticking off the U.S. government in the process. Eventually, the government sends another armor after him in Firepower, which “kills” this version of Iron Man once and for all, leading to Stark pretending to hire another person to wear the suit.

5 EXTREMIS

iron man extremis

For years, one thing which set Stark apart from other heroes was the fact that underneath the armor capable of superhuman feats, there was merely a man. But after battling against an individual enhanced by the virus known as Extremis, Stark realizes he needs to take the next step towards the future. Rewriting the techno-virus himself, Stark injects himself with Extremis and completely rewrites his biology. Extremis allows him to control his armors with his own brain instead of using artificial intelligence, and allows him to “summon” the armor telepathically. Stark enjoys these powers for most of the 2000s until he’s shut down with a different virus, causing him to undo Extremis on himself.

4 LEADING THE SUPERHUMAN REGISTRATION ACT

In 2005 a group of inexperienced heroes working on a reality television series for their adventures wind up handling a supervillain incident poorly, leading to the death of 600 people in Stamford, Connecticut. This event would kickstart a superhero “civil war” that would split the community in two directions: one side believing heroes should register their identities and become licensed agents of the government, with the other side wanting to keep things as they were for fear of government abuse. Stark would become the champion of the Superhuman Registration Act, hoping to ease the tensions between heroes and the world by behaving responsibly. It would be a decision which would cause problems for him for years to come.

3 BECOMING DIRECTOR OF SHIELD

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In the aftermath of the Civil War event, Tony Stark doesn’t just become the main person supporting the Superhuman Registration Act. He’s “rewarded” for his decisions by taking over as Director of SHIELD after Nick Fury vanishes. In this role, he’s given complete control over all superhero related operations, and is allowed to create a government sanctioned version of the Avengers, known as the Mighty Avengers. Stark has this role for just over a year until his technology is attacked en masse by the Skrulls and he’s largely ineffective during the battle against him. As a result of the entire world seeing Norman Osborn take out Veranke, Queen of the Skrulls, control of SHIELD is handed over to him, leaving Stark ousted.

2 DISCOVERING HE WAS ADOPTED

During the “Secret Origin of Tony Stark” by Kieron Gillen, Greg Land, and Dale Eaglesham, Stark learns that he was actually not the birth son of his parents Howard and Maria. Though Stark would meet Arno, the actual son of Howard and Maria during Gillen’s run, it wouldn’t be until years later he would finally come face to face with his own mother. Named Amanda Armstrong, Tony would learn he got his need to do a million things at once from her, as she turned out to be a rock star who became a secret agent. She gave up her child after realizing Tony’s father was actually working for Hydra.

1 BECOMING A SYNTHETIC BEING

This one’s a little weird. Between the aftermath of both Secret Invasion and Civil War II, Tony Stark had to deal with quite a bit. To protect the secret identities of the heroes from Norman Osborn, he winds up manually deleting all of his brain data and restoring it via a digital copy. Then, thanks to a battle with Captain Marvel in Civil War II, he winds up in a coma while his body completely reboots itself. With both his body and mind having been completely reset and started from zero, Stark is now left wondering if he’s even human at all anymore.

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