Most terrible things Iron Man has ever done

Neither Batman nor Iron Man have any powers, and they both rely on a combination of gadgets and smarts to survive, but that's where the similarities end. See, while Bruce Wayne pretends to be an arrogant, womanizing cad, Tony Stark actually is one—not to mention a recovering drunk, a reckless businessman, and an on-again off-again supervillain.

Sure, we all love Iron Man thanks to Robert Downey, Jr.'s pitch-perfect performance, but take away the Hollywood charm and Tony's true personality comes out. When Mr. Stark is left to his own devices, he's usually up to no good, and even his best ideas usually end up as a disaster for either Tony or his allies. Being Tony Stark's friend is a lot like putting yourself in the line of fire—and more often than not, it's Iron Man himself who's pulling the trigger.

He sold weapons of mass destruction

Let's get this out of the way early: according to Stan Lee, Tony Stark was never supposed to be a good guy.

"It was the height of the Cold War. The readers, the young readers, if there was one thing they hated, it was war, it was the military. So I got a hero who represented that to the hundredth degree," Lee said in an interview tied to the first Iron Man film. "I thought it would be fun to take the kind of character that nobody would like, none of our readers would like, and shove him down their throats and make them like him."

When we first meet Tony Stark in 1963's Tales of Suspense #39, he's not a hero—he's a self-centered industrialist who's using the Vietnam War to make a quick buck. As the story opens, Stark is peddling "tiny transistors" that are powerful enough to break a safe wide open. When he's captured by Wong-Chu, a Vietnamese warlord, his weapon-making prowess is so well-known that Wong-Chu puts him to work almost immediately.

Unlike the Iron Man movie, Tony doesn't stop making weapons when he returns home, either. In Tales of Suspense #40, he's hawking engine-powered roller skates to help troops move without the need for other vehicles. In the next issue, he tells his date he'll never get married because he's too busy making devices like atomic naval cannons—which launch nuclear missiles further than any other device, and burp guns that turn regular bullets into heavy artillery. Iron Man himself may not kill, but Tony Stark's machines have taken plenty of lives—and made their inventor filthy rich while doing so.

He superheroed while drunk

Iron Man doesn't have a deep and varied rogues' gallery like Batman, Spider-Man, or Superman—but he doesn't need one. Tony Stark has always been his own worst enemy, and his alcoholism will always be his number one nemesis.

Tony drank on the job almost as soon as he appeared—as a jet-setting executive in Mad Men's swingin' '60s, it was practically a job requirement—and in Iron Man #120, the beginning of the acclaimed "Demon in a Bottle" arc, he shows no signs of slowing down. After all, he says, he's "drinking for two"—both Tony Stark and Iron Man, who most people assume is Stark's bodyguard. When Iron Man's armor starts malfunctioning and S.H.I.E.L.D. starts a hostile takeover of Stark Industries, Tony deals with the stress by pounding champagne and cocktails. When Justin Hammer takes control over Iron Man's suit, killing a foreign ambassador and forcing Tony to hand his armor over to the police, a bottle of Napoleon Brandy is there for him, even if his friends aren't.

While many people suffer from addiction, few of them wear one of the most deadly weapons in the world to work. Tony deals with Hammer and clears Iron Man's name, but the booze doesn't disappear quite so easily.

Intoxicated, Tony cheats on his girlfriend Bethany and chews out his faithful butler, Jarvis, forcing the latter to hand in his resignation. After a couple more shots, Tony straps on his armor and takes to the skies for an impromptu booze cruise, but only manages to make things worse when he spreads a cloud of toxic fumes over a dense crowd. Eventually, Bethany and Jarvis help Tony kick his addiction, but not before Tony does quite a bit of damage—something that he'll do again and again as he struggles to stay sober.

He attacked soldiers, government agents, and Captain America

Many people dislike Tony Stark, but almost everyone wants a piece of that sweet, sweet Iron Man armor—especially Justin Hammer, head of Hammer Industries and Stark's chief rival. In the late '80s "Armor Wars" storyline, Hammer almost gets what he wants, too, forcing Tony to go to extreme measures to reclaim what's rightfully his.

In Iron Man #255, Tony learns that, thanks to his carelessness, supervillains are using stolen Stark Industries technology to make themselves more powerful. Even worse, the man behind the theft—Hammer, of course—is too well-protected for law enforcement agencies to get him, leaving Iron Man to take out anyone who's using his technology by himself.

Given how rarely Tony Stark makes the right decisions, things go about as well as you'd expect. In the next issue, Iron Man goes after the hero Stingray, who's not only not using Stark Industries designs in his armor, but also happens to work for the United States government. As authorities demand Iron Man's resignation, Tony gives S.H.I.E.L.D. false information about Iron Man's identity, and then springs a trap on S.H.I.E.L.D.'s Mandroid army.

Over the course of his crusade, Iron Man assaults and almost kills the Guardians, who work as prison guards, beats up Captain America, inadvertently kills a Russian superhero, gets kicked off of the West Coast Avengers, and takes a nuclear missile to the chest. All that, and at the end of the day, it doesn't actually do much good: everyone who died thanks to Stark Industries tech is still dead, and all Tony can do is wallow in his own guilt—and try not to pour himself a drink.

He murdered fellow Avengers and tried to destroy the world

Rita del Mara, better known as the hero Yellowjacket. Marilla, an Inhuman babysitter. Amanda Chaney, publicist for the superhero team Force Works. In The Crossing, Tony Stark kills all three of them. He would've gotten away with it, too, if he hadn't forgotten the most important rule when committing murder: don't leave any witnesses behind.

Iron Man's crime spree begins when Yellowjacket crashes an Avengers reunion and attempts to warn the super team about Stark's upcoming betrayal. Unfortunately for Rita, Iron Man finds her first. With a single blast of his repulsor beams, Tony silences Yellowjacket for good, and then rejoins the party—without realizing that Luna, the daughter of Quicksilver and the Inhuman royal Crystal, is watching from the shadows.

As the bodies pile up, Tony tries to pin the crimes on Hawkeye, but the jig is up when the Avengers put Luna into an Image Inducer, allowing them to observe her memories. Tony puts the Wasp in a coma (or, technically, a cocoon), and then flees to an armored bunker in the Arctic. Meanwhile, the other Avengers learn that the time-travelling villain Kang the Conqueror has been manipulating Tony since he first became a superhero, slowly brainwashing Iron Man and turning him to Kang's side. An assault on Iron Man's bunker almost costs the Vision his life, and the Avengers realize that the only person smart enough to stop Tony Stark is, well, Tony Stark.

In response, a group of Avengers head into the past, teaming up with a 19-year-old Stark—before Kang got his hooks into the boy—and bringing him to the present. With young Tony's help, they break into Iron Man's bunker and stop Kang, but not before the present-day Iron Man dies, passing on the mantle to his younger self (and if you thought adult Tony Stark was obnoxious, just wait until you see what he was like as a teenager).

He humiliated his friends in front of the United Nations

During his brief tenure as Secretary of Defense, Iron Man made many mistakes, but his biggest and final blunder occurred in Avengers #500, when Tony Stark gave a speech to the UN while totally and completely wasted. While speaking about the future of international superheroics, Tony suddenly and violently turns on the representative from Latveria (Doctor Doom's home country), calling him a piece of garbage, proposing to bomb Latveria off of the map, and then powering up his repulsor and threatening to murder the man in cold blood.

T'challa, the Black Panther, comes to the delegate's rescue, but it's fellow Avenger Hank Pym who bears the brunt of Tony's attack. As security escorts Tony off of the stage, Pym tries to make sure Stark is okay, inspiring Tony to yell out, "Shhhut up… don't you have a wife to beat?" in front of the entire delegation. Later, Tony admits to the Scarlet Witch that he's drunk—even though he hasn't had a single sip of alcohol.

It's all the Scarlet Witch's doing, of course. Driven insane by the loss of her children, she's lashed out and used her powers to tear the Avengers apart, making Tony magically drunk in the process. Still, while the booze might've been imaginary, Tony's words aren't, and he's forced to resign as Secretary of Defense as punishment for embarrassing both his friends and his country.

He shot the Hulk into space

As a member of the Illuminati, a secret cabal of Marvel's smartest and most powerful superheroes, Tony Stark doesn't always commit his terrible acts alone. When Captain America warned the Illuminati not to build an Earth-destroying superweapon in the lead up to 2015's Secret Wars, Tony and Doctor Strange erased Cap's memory. When the Illuminati trick the Hulk and sentence him to a life in space, however, that's all on Mr. Stark.

After the Hulk levels Las Vegas and kills 26 people—including a couple of children—and a dog, S.H.I.E.L.D. director Maria Hill reaches out to Tony and asks him do something about Bruce Banner's rampaging alter ego. He does.

With the Illuminati's help, Tony puts together a plan to rid the world of the Hulk for good: they'll use a Life Model Decoy to impersonate Nick Fury and get Bruce Banner on a spacecraft, where he'll be in charge of fixing a satellite using the Hulk's super-strength. Once the Hulk is beyond the atmosphere, however, the Illuminati will redirect his ship and send him to an empty planet, where the Hulk can live out the rest of his days alone, without potentially hurting anyone.

It's cruel and unusual punishment for sure, and it gets worse. Hulk's ship gets lost along the way, and the Jade Giant ends up crashing on the planet Sakaar, a hostile and extremely populated planet. Hulk eventually conquers Sakaar—yes, the whole thing—and then returns to Earth, takes over Manhattan, and sets out to get revenge on Stark and his friends.

He started two superhero civil wars

In 2006, war broke out in the Marvel Universe. On one side, Captain America led a group of superheroes opposed to the Superhuman Registration Act, which would force America's finest to reveal their secret identities and work under the government's supervision. On the other, Iron Man and S.H.I.E.L.D. started rounding up superheroes who failed to comply with the Act and locking them up in the Negative Zone.

In the Civil War marketing materials, Marvel asked fans to "choose a side," but it's pretty clear Iron Man is the bad guy in this story. In order to drum up support for the Registration Act, Tony convinced Peter Parker to reveal his secret identity to the world, which ended up almost costing Aunt May her life and turned Parker's life into such a mess that he had to make a deal with the literal devil to make it go away. While debating the Registration Act's merits with Iron Man, Luke Cage likens it to slavery. In Civil War's aftermath, Tony Stark becomes the director of S.H.I.E.L.D. and Captain America is dead. That's symbolism, and it isn't subtle.

You'd think after all of that, Tony would've learned his lesson, but no. Later, Carol Danvers (better known as Captain Marvel) starts using a psychic's visions of the future to stop crimes before they happen—even if that means capturing or killing people who haven't actually done anything wrong. In protest, Iron Man rounds up his friends and declares war on Carol and S.H.I.E.L.D, and while Iron Man is ostensibly the hero in this story, things go even worse for him the second time. When the dust clears, Tony Stark is stuck in a coma, while Captain Marvel has carte blanche to reshape the superhero community as she sees fit.

He created a psychopathic Thor clone

Of all of the terrible things Tony Stark does during the first Civil War, cloning one of his closest friends and using the results to kill a beloved superhero is near the top of the list. In Civil War #4, Thor—who has been dead for a while—shows up during a battle between Iron Man's pro-registration forces and Captain America's rebels and blows a hole through Black Goliath with his lightning.

Except it's not actually Thor at all, but a clone named Ragnarok (or "Clor," according to some fans) developed by Stark, Reed Richards, and Hank Pym. While all three heroes get their share of the blame for Black Goliath's murder—Sue Storm leaves Reed as a result of his role in the debacle—it's clear that Iron Man is the real brains behind the operation. See, Hank Pym says Tony has been holding onto a strand of Thor's hair since the very first time the Avengers met.

In the aftermath, Pym asks, "What kind of man combs his furniture for hair follicles and skin cells?" The Wasp replies, "One with a lot of foresight," really getting to the crux of the problem: not only did Tony defile his friend's memory and kill one of his former allies, but even worse, he'd been planning the whole thing for a very long time.

He deleted his mind instead of dealing with his problems

After the drunk shenanigans with the Avengers, the Hulk's exile, and the first Civil War—as well as an alien invasion that occurred while he was the head of S.H.I.E.L.D., which also happened to disable Stark technology and ruin the Stark Industries brand for good—Iron Man has a lot to answer for. Instead, he runs away. Oh, sure, Tony says he deleted his memories in order to keep the superhero registration database (which he'd previously uploaded directly into his brain) out of Norman Osborn's hands, but as the "World's Most Wanted" storyline shows, it's really just an excuse for Tony to avoid facing any consequences for his actions.

It works, too. After spending months getting progressively dumber, which makes it harder and harder for Iron Man to defeat Norman Osborn, Tony falls into a vegetative state. Thankfully, Stark stored his mind on a hard drive and gave his friends instructions on how to "reboot" his brain. Conveniently, however, Stark made the backup well before the superhero Civil War started, meaning that Tony doesn't remember any of his heinous actions during the conflict and is able to live the rest of his life guilt-free.

Oh, and did we mention that while his mind was slowly deleting itself, Tony slept with both Maria Hill and Pepper Potts, knowing full well that his failing memory meant that he'd be able to avoid any future love triangles or romantic entanglements? Yeah, a real stand-up guy, that Tony Stark.

He got people addicted to his software and then charged them money for it

In Marvel's big "AXIS" storyline, the company's characters had their moral compasses flipped, turning villains into heroes and heroes into villains. At the end of the event, most of them flipped back. Tony Stark didn't.

Instead, Stark drops his body-altering Extremis tech in San Francisco's water supply, making anyone using the Extremis smartphone app strong, healthy, and beautiful. But there's a catch: once the poor San Franciscans get a dose of perfection, Tony takes Extremis away. If the citizens of the City by the Bay want to continue using the software, they'll need to give Tony Stark $99 a day to do so.

As a result, San Francisco's citizens start discriminating against those without Extremis based entirely on their looks, while people who became addicted to perfection will do almost anything, legal or otherwise, to get it back. As for Tony, he spends most of his time drinking, doxxing his critics, brainwashing Daredevil, and carousing in the lavish headquarters he built on Alcatraz Island.

Pepper Potts and an artificial intelligence based on Tony's own mind team up to take the Superior Iron Man down, but they don't succeed. Tony uses the Extremis tech to turn his customers into living shields, then manipulates Pepper's emotions to sneak into Stark Resilient and inject a virus into the system, destroying the AI Iron Man for good. In fact, the only reason Tony Stark is a good guy today is Marvel's 2015 Secret Wars, which ended in the destruction of the universe. That's right: in Superior Iron Man, Tony Stark is so evil that the only way to beat him is to rewrite reality itself. Yikes.