Everybody’s favorite genius billionaire playboy philanthropist has saved the world many times over, both by himself and alongside his fellow Avengers. Yet at his core, Tony Stark, aka Iron Man, remains a deeply flawed human being. For every heroic trait he possesses, like loyalty to his friends, there’s an equally unsavory one that exists within him, such as his complete lack of humility.

Marvel Studios’ blockbuster movies starring Robert Downey Jr. have elevated Iron Man to incredible new heights, mixing snarky humor with know-it-all brilliance in just the right amounts that we always root for him. The actor’s impossible charm has made him far and away the most beloved adaptation of the character, but Tony hasn’t always been a good man in the comics. In fact, there have been many times when he stopped tiptoeing the line between right and wrong and came off as downright villainous.

Here are 15 Times Iron Man Was Basically A Villain.

15. That time he kidnapped an Inhuman

Iron Man kidnaps Ulysses 15 Times Iron Man Was Basically A Villain

Our first example of Mr. Stark being bad is the most recent. At the outset of 2016’s Civil War II, a new Inhuman surfaced with the seeming ability to see the future. This new hero, a college student named Ulysses, was immediately added to the Inhuman society, but Tony Stark, being Tony Stark, had a hard time accepting Ulysses’ predictions at face value.

No one would listen to his concerns — which were based on the fear that Ulysses’ own opinions and biases could alter his visions — and when Tony’s best friend was killed on a mission that was inspired by a new vision from Ulysses, the situation was more than he could stand. So he did the logical thing. Logical, that is, if you’re Tony Stark.

He broke into the Inhuman city Attllan and absconded with Ulysses against the young man’s will. It provoked an international incident, naturally, but all Tony cared about was figuring out how Ulysses’ brain worked. He ran some scans on the boy and tried to provoke a vision by frightening him. Predictably, it didn’t end well for Iron Man, who was stopped by a huge group of his friends. It’s mostly played for laughs in Civil War II #2, but you can’t deny that taking someone against their will is not just wrong, it’s against the law.

14. That time “Iron Maniac” invaded

Iron Maniac a villainous Tony Stark from another dimension 15 Times Iron Man Was Basically A Villain

In 2005, a story arc in Marvel Team-Up saw Spider-Man, Captain America, Black Widow, X-23, and a young superhero named Freedom Ring, team up to take on a villain new to the Marvel 616 universe: Tony Stark. Only it wasn’t their Tony Stark, it was an invader from an alternate universe (Earth-5012).

This Earth was ravaged by a war against Titannus that saw many heroes die. Hardened and embittered by so much death, this Tony became a different kind of Iron Man: a brutally violent man with a compromised moral compass. When his Reed Richards sent him to Earth-616, the Fantastic Four mistook Tony-5012 for Doctor Doom, since he was wearing a green suit of armor similar to his archenemy’s. Iron Man-5012, meanwhile, was super pissed to see Johnny Storm, who in his dimension had burned his face to disfigurement.

After everyone figured out who this newcomer was, Tony-5012 escaped and impersonated the real Tony Stark to procure supplies. He tried his best to get home, but the team-up group stopped him, and he was imprisoned. Sometime later he escaped, dubbed himself “Iron Maniac,” and built a new suit of armor. He was last seen getting his head bashed in by Captain America, but he’s still alive, presumably in S.H.I.E.L.D. custody.

13. All the times there were evil Iron Men in Exiles

An alternate villainous Iron Man appears in Exiles 15 Times Iron Man Was Basically A Villain

In case you’re not familiar, the Exiles were a team of alternate Marvel superheroes from different dimensions and timelines. The group’s makeup was constantly changing, with old members leaving or dying and new members joining up. Noteworthy members have included alternate versions of Scarlet Witch, Black Panther, Beast, and many more. Together, they traveled across multiple realities, fighting those who sought to do irreparable harm to the multiverse and their own dimensions.

Throughout its run, which began in 2001, this oddball team encountered numerous versions of Iron Man, and every time… Well, even with the better Tony Starks, it’s safe to say they didn’t play nice together. Most of them were just outright bad guys.

Take the one from Earth-2020, who started a world war in his own dimension, as well as being part of an alternate Exiles team made up of villains. Things got worse in a later story arc, when another Tony Stark became the ruler of his world and killed almost the entire superhero population on his Earth. And even when there was a bona fide good Iron Man on another world, he was killed by the Hulk, and it fell to the Exiles to find a suitable replacement. Instead of bringing in an alternate Tony Stark, as they might have with another superhero, they installed Spitfire in his place.

12. When he was an arms dealer

Tony Stark as head of Stark Industries 15 Times Iron Man Was Basically A Villain

If not for the original Iron Man movie, most fans might not even remember this. Before he became Iron Man, Tony Stark manufactured and sold advanced weaponry to anyone who could afford them. The business was started by his father, Howard Stark, but when both his parents were killed in a car accident, Tony inherited the company and carried on its business. Some might argue that selling weapons is evil in and of itself; everyone else might at least agree that not discriminating in who you sell them to can only lead to malevolent consequences.

To be fair, Tony also expanded Stark Industries into a technology manufacturer of all kinds, such as personal electronics and forward-thinking scientific advancements. Despite this, weapons sales continued, and it was during one of these sales in an active war zone that he had the famous accident that led to his captivity and subsequent construction of his first Iron Man suit.

If you can believe it, even this life-altering incident didn’t cause him to see the light. Tony actually planned to manufacture his Iron Man suit en masse and sell it to the public. Imagine the devastation that could have been caused. Fortunately, an incident of theft finally made him realize that millions of people walking around in their own weaponized suits of armor might not be the bestest idea ever.

11. That time he was a cyborg killing machine

Alternate Iron Man named Steel Corpse 15 Times Iron Man Was Basically A Villain

A 2011 crossover miniseries (and some requisite tie-ins) introduced Marvel fans to Earth-11326. This was Age of X, a reality where mutants were considered dangerous and evil, and had been hunted to near extinction. Even other superheroes, who usually defend mutants on Earth-616, hated them and joined in the hunt.

A team of Avengers on Earth-11326 was tasked with stopping mutant threats, and one of them was a character who called himself the Steel Corpse. This was Tony Stark, a mysterious figure whose body had been bonded to his armor via some kind of disease — which of course, mutants were blamed for. Making matters worse, the suit was literally eating him, consuming his body thanks to said disease.

The Steel Corpse spoke in an odd fashion, combining both a computerized voice with a human one, resulting in a particularly dark sense of humor. By the time Age of X took place, he was already more machine than man, being describing in the comics as “unstable.” That’s an understatement, to say the least. In his first appearance, just after Captain America had arrested a mutant, Tony forewent justice and killed the guy on the spot.

10. When he became president after cheating in Civil War

President Tony Stark from Contest of Champions 15 Times Iron Man Was Basically A Villain

After Secret Wars ended, the pocket dimension the whole thing took place in remained more or less intact, and was subsequently occupied by Maestro, the alternate, much older, and genius-intellect version of the Hulk. Hijacking a gladiator-style game that had been set up by the Collector and the Grandmaster for displaced superheroes from across dimensions, the villainous green guy wrested control of the game and a powerful artifact called ISO-8, with which he was able to shape reality. This all occurred in a 10-issue 2015 miniseries called Contest of Champions.

Maestro reconstituted Battleworld, and one of the realms on the patchwork planet was a United States where Iron Man won Civil War (which we’ll get back to later) some five years prior, and Captain America and his allies were fitted with death collars and put to work as the Thunderbolts. Things went swimmingly for Tony Stark from the start of the War, and after he won, he became the Iron Patriot and was installed as President of the United States.

As it turned out, the reason everything went Tony’s way was that he couldn’t lose. He’d been using the Reality Stone — one of the six Infinity Stones — to ensure his victory. In short: he cheated. It started small, restoring Bill Foster to life after he was killed by Thor’s clone, for example. But the power corrupted him, and he used it to seize the presidency. Anyway, the Reality Stone didn’t work on Battleworld because it was from another dimension, and Maestro arrived to literally squish Tony to death.

9. That time he cloned Thor

Thors clone Ragnarok from Civil War 15 Times Iron Man Was Basically A Villain

You know the story. A superhero Civil War kicked off after a team of undertrained supers inadvertently caused the deaths of 600 civilians in Stamford, Connecticut — 60 of whom were school children. Public opinion of superheroes turned against them, and sides were drawn around the Superhero Registration Act.

The SRA, an official U.S. law, mandated that all superheroes had to be registered with the government like policemen. Iron Man and his followers believed the SRA was a way of legitimizing their work; Captain America and his team saw it as a form of indentured servitude, and a severe invasion of privacy, since registered heroes were required to reveal their real names.

During Civil War, the tide of history was on Tony Stark’s side in our post-9/11 world. But in trying to “do the right thing,” Tony made a number of highly questionable decisions. One of them was using a strand of Thor’s hair — which he’d saved after the first-ever meeting of the Avengers — to clone the believed-dead God of Thunder. Not only would the real Thor have seen this as an offensive violation, this construction of genetic material and cybernetic lacked the Asgardian’s moral center. During one of the most brutal fights of the War, the clone showed up, kicked pretty much all of the butts, and then blew a hole straight through the chest of Bill Foster, aka Goliath, killing him in an instant.

Probably not Tony’s proudest achievement.

8. When he co-founded the Illuminati

The Illuminati 15 Times Iron Man Was Basically A Villain

There’s no denying that this one falls under the banner of more than just Tony Stark. But the whole thing was his idea. Sometime after the Skrull-Kree War, which nearly destroyed the Earth, it occurred to Iron Man that had the superheroes of the world worked closer together, sharing information and resources, they might have stopped the war before it began.

So he called together a meeting of himself, Doctor Strange, Reed Richards, Professor X, Black Bolt, Namor, and Black Panther, a group met privately in Wakanda. There, he proposed his idea: anytime a really big issue came up that could affect the entire world, they would call a meeting and collaborate to find the best possible solution. Dubbed “the Illuminati,” they would operate in secret, known only to one another, for years.

It sounds okay on the surface, but it would only be a matter of time until an issue came up that would require them to undertake actions with very sketchy morals. And they would be performing these unilateral actions while keeping everyone they know and love in the dark. In the words of Black Panther, who refused to sign on with the group, “You just decided all by yourselves that you are the Earth’s protectors. And that you, and only you, not your teammates or family, are trustworthy enough to include in the process.

7. That time he got Spider-Man to unmask publicly

Iron Man unmasks Spider Man as Peter Parker during Civil War 15 Times Iron Man Was Basically A Villain

Just prior to Civil War, Tony Stark had been acting as a mentor to Peter Parker. The New Avengers had been formed not long before, and when Peter and Mary Jane’s home was destroyed by one of his enemies, Tony invited them to live in Avengers Tower. Tony then built Spidey a new suit, which was tricked out with all kinds of high-tech goodies.

So when the winds of Civil War‘s change started blowing, it wasn’t hard for Stark to get Peter Parker to sign on with the Superhero Registration Act. Not content to stop there, Tony pressured and manipulated Peter into undertaking an unprecedented action, an action Tony hoped would convince more heroes to sign on.

In an infamous scene that “cracked the Internet in half,” the end of Civil War #2 saw Tony Stark introduce Spider-Man at a press conference. The web-slinger took the stage and promptly removed his mask, telling the whole world who he really was. It probably seemed like a good idea to Peter at the time, but it wasn’t long before he regretted this decision. It ultimately put Aunt May’s life in danger, resulting in Peter and MJ bargaining with the devil to erase their marriage from history and pissing off a huge number of Amazing Spider-Man readers. Adding salt to the wound: Tony had used Peter’s time in the “Iron Spider” costume to spy on the younger man and collect physiological data about him.

It was pretty much a dick move across the board.

6. That time the Illuminati exiled Hulk from Earth

Hulk is sent away from Earth by the Illuminati 15 Times Iron Man Was Basically A Villain

One of the earliest things the Illuminati did was one of the worst ideas they ever had. Under pressure from S.H.I.E.L.D. to find a solution to the Hulk problem after the big green guy decimated Las Vegas, Tony called a meeting of the elite superheroes and made a drastic proposal.

He suggested that they find an uninhabited world somewhere in the cosmos, put the Hulk in a spaceship, and launch him away from Earth and toward that planet. There, he could live out his days in peace while the people of Earth would be safe from his rage. It didn’t go quite as planned.

Namor alone objected to the whole idea, pointing out that Bruce Banner was their friend and colleague and that it was wrong of them to do this to him. He and Tony had words — and fists — and ultimately Namor walked away from the group before warning them that one day Hulk would return seeking revenge. And he would be in the right to do so.

A few years later, he was proven correct.

5. When he built a prison for superheroes

Iron Mans Prison 42 15 Times Iron Man Was Basically A Villain

Back when Tony Stark and his buddies Reed Richards and Hank Pym were all gung-ho for the Superhero Registration Act, they sat down together and brainstormed a list of really big ideas. Supposedly, there were one hundred of these ideas, and each one was meant to make the world a better place that people could feel safe in, with ideas for things like the environment, global poverty, defense, and more.

The only one of these ideas that’s ever been identified as such is number 42, which was a massive prison built in the Negative Zone — that weird alternate dimension that the Fantastic Four tend to visit a lot — to hold supervillains. The problem was that once the prison was built, Iron Man and his super-registered pals decided to use it to hold unregistered superheroes in addition to all the bad guys that had been captured.

Captain America led a massive prison break at the climax of the Civil War, with every captured hero — and even some of the villains — escaping to join Cap’s side of the fight. After the war ended, Tony Stark & Co. abandoned Prison 42. The law may have been on his side during the War, but it’s hard to get past the feeling that putting your friends in a maximum security prison in another dimension — which Susan Storm described best as a “hellhole” — is just a crummy thing to do. Very few of the people imprisoned there actually deserved it.

4. That time he let himself be evil

Superior Iron Man Wallpaper 15 Times Iron Man Was Basically A Villain

So once upon a time, a bunch of heroes and villains had their personalities inverted. (It’s a long story.) Everyone caught in the effect took on traits that were opposite of those they’d always had. For example, the X-Men turned evil, deciding that mutants should drop all that wishy-washy “trying to live peacefully with humans” business in favor of ruling over them. Carnage became a superhero. Deadpool became a pacifist called Zenpool. Doctor Doom tried to turn Latveria into a democracy. You get the idea.Tony Stark was among those affected by the moral inversion, and the result in his case was a return to the greedy capitalist he’d been before becoming a hero.

Tony Stark was among those affected by the moral inversion, and the result in his case was a return to the greedy capitalist he’d been before becoming a hero. He moved to San Francisco, and modified the Extremis virus into a drug (accessible via smartphone app) that anyone could use to make themselves beautiful, highly intelligent, in perfect health, and forever young. But much to everyone’s surprise, at the end of the app’s first day, its “trial period” was over, and that if people wanted to continue their Extremis-enhanced lives, they would have to pay Stark Industries $99.99 a day.

Admittedly, most of this wasn’t his fault. The magic spell that was cast to invert personalities and morals was beyond his control. But when a counter-spell was activated, Tony used a shield in his suit to protect himself from reverting to normal. And that pretty much was his fault. This new, immoral Tony Stark’s adventures were chronicled in the pages of Superior Iron Man, a 9-issue series where Tony sported one of his craziest Iron Man suits ever. It ended when Pepper Potts exposed his activities to the public.

3. That time he had supervillains hunt down his friends

Thunderbolts from Civil War comic 15 Times Iron Man Was Basically A Villain

We have to go back to Civil War one last time, but this is the worst part of all. Was it one of his “100 ideas” to have villains hunt down and round up unregistered superheroes? It was never verified, but likely so.

After the Superhero Registration Act was passed and a whole mess of superheroes went underground with their heroics, Iron Man turned to the Thunderbolts to track down those heroes and bring them to justice. And not just any Thunderbolts — he stacked the team with the worst, most bloodthirsty villains he could find. The very notion of forcing villains to do good is one that’s been touched on many times in comics and movies, and the morality of it is open for debate. But this instance was a little different.

The best example of this is probably what happened to Spider-Man. Having seen the error of Iron Man’s ways, Peter Parker decided it was time to jump ship and join Captain America’s side of the debate. Tony didn’t let him go without a fight, though Spidey managed to get away (albeit with some injuries). But that was nothing compared to what happened when Jack O’Lantern and the Jester were assigned to track him down. In the ultimate irony, two of the web-slinger’s own villains were lawfully hunting him, fighting him, and gravely wounding him. He would have been killed had the Punisher not intervened.

2. When he was possessed by Immortus

Iron Man being possessed by Immortus 15 Times Iron Man Was Basically A Villain

There’s nothing like an old fashion case of possession to turn a good guy bad. In 1992, a baddie called Immortus (who was actually a future version of Kang the Conqueror — don’t ask) began to influence Tony Stark’s mind. It started as xenophobia, but grew to the point that eventually, Tony undermined the efforts of his teammates and even murdered three people to keep his secret.

A long, slow-burn buildup culminated in Iron Man #323, where a psychic probe finally revealed the truth: that something had been influencing Tony, affecting and changing him for a very long time — for years, in fact. Immortus was playing a very long game to take down the Avengers from the inside.

It ended with the ridiculous notion of bringing a teenage Tony Stark (who was supposedly untouched by Immortus’ corruption) forward through time to replace his older, damaged self. It was part of an initiative to make Iron Man hipper, cooler, and more accessible to younger readers. It didn’t work out well, and after a series of convoluted events, the original Iron Man was restored, and everything went back to normal.

1. That time he destroyed a bunch of alternate Earths

An Incursion the collision of two worlds 15 Times Iron Man Was Basically A Villain

Over several years, writer Jonathan Hickman conceived of and executed a long-term storyline that found alternate Earths throughout the multiverse colliding with one another, resulting in the annihilation of both. Over and over it happened, and it wasn’t long before Earth-616 was threatened by these “incursions,” as they were dubbed.

The Illuminati, faced with an impossible choice, had to figure out what to do when the incursions threatened Earth. What could they do but try to preserve their own Earth — even if it meant destroying the one it was on a collision course with? But how could they possibly destroy an entire world, and the billions of innocent people living there? To protect themselves and their world, they chose genocide. It was a fateful decision that led to the collapse of the multiverse and the events of Secret Wars.

How many Earths did they destroy to save their own? It’s not clear if Marvel ever put a number to it, but it’s safe to assume that it’s somewhere over ten. Quite possibly a lot over ten. Maybe “they did what they had to do,” and Iron Man certainly didn’t act alone. But as villainy goes, destroying entire inhabited planets is pretty hard to top.

When else has Tony Stark flat-out behaved like a bad guy? Let us know in the comments.

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