It’s impossible to be a superhero for any real length of time without developing a sizeable grouping of rogues, whether they want revenge, to make a name for themselves, or just because the hero stops them from trying to take over the world or wipe out everyone. Unfortunately for Iron Man, he has managed to garner enemies both in his superhero identity and as Tony Stark back when he was keeping both worlds separate. As CEO of Stark Industries, Tony Stark managed to gain quite a few enemies, from business rivals taking the phrase “taking out the competition” a little too literally, to former employees turned evil, to anti-capitalists and corporate saboteurs who want to take out the man who was once head of the biggest munitions corporation in the world.
On the other end of that, you’ve got Tony Stark’s life as Iron Man. Despite posing as a mere bodyguard for himself, Iron Man managed to create quite a few enemies all on his own, long before it was revealed they were one and the same people. The Mandarin only ever seemed interested in Tony Stark insofar as how he could use him to get at Iron Man. And thanks to Iron Man’s roots as a Cold War-era creation, both the Titanium Man and Crimson Dynamo were only interested in their ability to shut down Iron Man to prove the superiority of Communist technology. Still, no matter their reasoning, we’ve got a collection of some of the most dangerous villains Iron Man’s ever run into over the years, and ranked them according to how deadly they’ve been to Ol’ Shellhead!
Firepower was the result of some of Tony Stark’s worst behaviors and attitudes coming back to bite him all at once. He’d ticked off a rival businessman known as Edwin Cord, and his quest to recover his stolen technology during the legendary “Armor Wars” storyline lead to a U.S. military project being repurposed specifically for the purpose of taking down Iron Man.
The suit was stronger and carried far more destructive weaponry than Iron Man expected, leading to Stark being absolutely decimated and his Silver Centurion suit being destroyed by Firepower’s surface-to-air missile. Fortunately Stark wasn’t in the suit when it happened, and his next model would have no trouble putting Firepower down.
Despite boasting one of the coolest costumes in Iron Man’s rogues gallery, Whiplash has never presented himself as much of a threat. Mark Scarlotti started out as a technician working for Stark, but because he wanted to enjoy the high life he decided to break bad, becoming a professional hit man for the Maggia, Marvel’s one time biggest criminal organization.
Unfortunately, things don’t have a happy ending for him -- the last time we saw him, he was dressed up in a creepy black leather outfit, and while he had a pretty close fight with Stark… when the Iron Man suit turned sentient it too out Mark for what looks like the final time.
18 LIVING LASER
Arthur Parks is by far one of Iron Man’s most enduring villains. He started out as a scientist, creating wrist-mounted laser projections and becoming a mercenary instead of just… selling that technology to the military for millions of dollars. Something of a creep, his first appearance involved him kidnapping the Wasp because he’d developed an obsessive “love” for her.
Eventually, Arthur’s laser tech got out of hand, transforming him into living energy. Still the character returned to plague both Iron Man and the Avengers multiple times in every decade since he was introduced in the '60s. Most recently he was seen in Bendis’ “Search for Tony Stark” story arc, trying to help The Hood get revenge against Doctor Doom.
17 GREY GARGOYLE
If you’d watched the '90s cartoon, it would be easy to believe Grey Gargoyle is primarily an Iron Man villain -- but he was first a part of Thor’s Rogues Gallery after his creation by Stan Lee and Jack Kirby in Journey into Mystery #107 in 1964. Once a French chemist, Paul Pierre Duval accidentally gained the ability turn any organic matter he touches into stone for an hour, as well as transform himself into stone to gain super strength.
His crowning battle against Iron Man was during the Fear Itself event, where one of the many hammers from Asgard transformed him into Mokk: Breaker of Faith. There, he not only easily trounced Iron Man, but turned the entire city of Paris into stone as well.
The Firebrand name has belonged to multiple characters since the original’s introduction in Iron Man vol. 1 #27 by Archie Goodwin and Don Heck back in 1970. For the most part, almost all of them have possessed similar backgrounds -- a strong activist background, and a firm belief that peaceful activism no longer gets the job done.
So it was from the very first Firebrand, a man named Gary Gilbert who ran into Iron Man when Stark was trying to invest in a community center against the wishes of a group of protestors. They got into it when Stark realized Firebrand’s thermo bursts could injure the crowd, and were bitter enemies until Gilbert was murdered by the Scourge of the Underworld, years later.
A Hungarian scientist, Gregor Shapanka was obsessed with immortality and believed the way to that goal was through the study of cryonics. He tried working for Stark Industries to fund his research, but was eventually sent to jail after trying to steal company secrets. Building a suit to let him generate cold, he called himself Jack Frost -- only to be taken to jail after kidnapping Stark’s best friends Happy and Pepper.
Eventually he would break free from prison and create an improved outfit and start going by the name Blizzard. After this, he nearly managed to kill Iron Man while trying to retrieve the Climatron, a device that would have granted him ultimate control over the world’s weather.
14 CRIMSON DYNAMO
Crimson Dynamo has been by far the most enduring armored villain Iron Man’s ever had. The person behind the mask changes time and again though, as there’s been over a dozen different Crimson Dynamos since the original one’s introduction in Stan Lee and Don Heck’s Tales of Suspense #46 in 1963.
Introduced as Ivan Vanko, the original Dynamo was a genius who even managed to create a suit slightly better than the Iron Man armor, running off a self-sustaining generator rather than constantly needing to be charged. Unfortunately, while the Crimson Dynamo has nearly defeated Stark several times over the years, the name is something of a curse with most of its users eventually winding up dead one way or another.
13 TITANIUM MAN
Alongside Crimson Dynamo, Titanium Man is one of the Soviet Union’s attempts to bring down Iron Man, proving the inferiority of capitalist-developed technology. Built off the blueprints of Ivan Vanko’s Crimson Dynamo armor, the Titanium Man armor was built to be stronger and more durable than the Iron Man armor, though this was largely due its inferior building materials.
Its first pilot, Boris Bullski, came up with the not so smart idea of challenging Iron Man to a one on one duel on national television. Eager to prove the superiority of his own engineering skills, Stark accepted, and wound up humiliating Boris in front of the entire world.
12 COUNT NEFARIA
Luchino Nefaria is easily one of the most powerful villains on this list in a walk. After allowing himself to be experimented on, Nefaria was granted absurd levels of super strength, speed, and energy projection strong enough to make him a danger to any and all superhero teams. That’s why early on Nefaria was just as much a generic Marvel Universe villain as he was an Iron Man rogue, as he had several run-ins with the Avengers as well as the X-Men.
But Stark’s closeness to his daughter Whitney Frost makes his battles with Nefaria particularly personal -- fortunately his largely unstable body made him a little easier to bring down than some of the other characters on this list.
11 EZEKIEL STANE
Son of one of the greatest villains Tony Stark has ever faced, Ezekiel Stane ultimately is never quite able to match up to the greatness of his father due to his obsession with Stark. Nonetheless, his improvements are quite impressive -- through his experimenting he manages to make his body efficient enough to only use seven percent of its caloric intake for day to day functions.
With the remaining 90, he’s able to run biological implants to upgrade his body to mimic that of the Iron Man armor. From there, he committed horrendous acts on Stark facilities all over the world with the help of soldiers willing to allow their bodies to be reprogrammed in order to have abilities on the level of Iron Man.
10 FIN FANG FOOM
Of all the villains Iron Man’s run up against over the years, the one villain no one would expect is a giant, extraterrestrial being that looks like a dragon. Nevertheless, he became a thorn in Iron Man’s side when he started working with the Mandarin after the longtime Iron Man villain believed he was a mythical dragon, and worked with him to conquer a third of China.
When it was later revealed Fin Fang Foom was actually an alien, he was left with no other choice than to work alongside both Iron Man and War Machine in order to avoid the entire planet being conquered by Fin and his fellow aliens.
Unlike many of Iron Man’s rogues, Temugin hasn’t had many run-ins with the Armored Avenger, but the times they have clashed have always been memorable. The son of the Mandarin, Temugin was handed over to Himalayan monks, never properly meeting his father for most of his life. His first run-in with Tony Stark came after his father mind-controlled him into trying to put an end to him.
By trying to shoot Tony in the chest, he would learn Tony was Iron Man. Later on, Temugin would inherit his father’s rings when it was believed the Mandarin was dead. With those, plus an ability to focus his chi to give him super strength, he very nearly defeated Iron Man once and for all.
It’s probably not surprising that one of Iron Man’s greatest villains is a giant robot. An android constructed by an alien race, Ultimo was meant to be their ultimate weapon of destruction, though when Iron Man first meets him he’s under the control of the Mandarin.
Probably Ultimo’s most well-known appearance came in the milestone issue Iron Man vol. 1 #300, where the giant android nearly laid waste to its surroundings if it hadn’t been held off by the “Iron Legion”, a group of Iron Man’s closest friends and former wielders of the Iron Man armor all wearing prior iterations and working together to stop the giant robot.
Ghost is an Iron Man villain people rarely think about, yet he’s managed to prove quite a threat to Stark, often when he was at his most vulnerable. Ghost’s biggest advantage seems to be that no one knows who he is… or how to capture him, thanks to his suit granting him both invisibility and intangibility.
The character has been a thorn in Tony Stark’s side since his introduction, but his most dangerous moment came during the "Stark Disassembled" storyline. After Stark purposefully lobotomized himself to stop Osborn from attaining the most dangerous S.H.I.E.L.D. information, Madame Masque hires Ghost to end him. Helpless and with no Avengers to aid him, Ghost very nearly manages to put a stop to Iron Man once and for all.
Spymaster has often proven one of Stark’s deadliest foes, with the first incarnation nearly successful in taking Tony Stark’s life with a well-aimed shot to the head, though fortunately it wound up being a Life Model Decoy. Later, he would be responsible for stealing Stark’s designs for the Iron Man armor and selling them to Justin Hammer, which would eventually lead to the infamous "Armor Wars".
But for all the damage the original did, the third Spymaster might have cost Stark the most. In his attempt to use Happy Hogan as bait to lure Iron Man into a trap, Happy Hogan saved his best friend by attacking the villain and causing them both to fall several stories to their untimely end.
5 MADAME MASQUE
Though she started out as rich socialite Whitney Frost, Masque’s life started going downhill the moment she learned she was the daughter of Count Nefaria, head of the mafia organization the Maggia. As a result, she lost her fiancée and delved into a life of crime, training to one day take her father’s place… until she finally runs into Iron Man.
After a few encounters on the battlefield, the two fell in love with one another, but when her father died due to an illness, Whitney turned on Stark and took her proper place as leader of the Maggia. She would butt heads with Stark numerous times, once even swapping bodies with Stark’s lover Bethany Cabe in order to assassinate him!
4 NORMAN OSBORN
You’d think a man who normally belongs in Spidey’s rogues gallery wouldn’t have wound up here. Yet, after Tony lost his spot controlling S.H.I.E.L.D. in the aftermath of "Secret Invasion", he became Norman’s primary enemy after they realized Stark kept the knowledge of all the biggest secrets of S.H.I.E.L.D. locked up in his head.
In the storyline, “World’s Most Wanted”, Stark spent almost an entire year on the run from Norman and his organization H.A.M.M.E.R., while he did his best to “zero out” all the information in his brain to make it unattainable by Osborn. It all ended with Stark barely functioning and wearing his original gray armor while Norman beat him silly in his Iron Patriot suit.
3 JUSTIN HAMMER
A rival entrepreneur, Justin Hammer was one of the first villains to hit Tony on a personal level. While Tony was still struggling with bouts dealing with alcoholism, Hammer found a way to hack into Tony Stark’s armor, causing it to malfunction at certain times before eventually taking complete advantage of the control he had by causing Stark to murder a foreign dignitary.
Hammer’s also responsible for giving most of Iron Man’s classic rogues an upgrade, funding their mercenary activities and paying them to take out his business rivals. Eventually he had Stark’s technology stolen and gave it away, causing the "Armor Wars", leading to Iron Man nearly perishing while trying to get his life’s work back.
2 OBADIAH STANE
Obadiah is easily one of the greatest villains ever to challenge Tony Stark. Intent on acquiring Stark Industries, Stane launches an attack on multiple fronts on Tony -- he locks him out of key contracts, has his own personal army, the Chessmen, attack him and even sets him up with Indries Moomji, a woman who turns out to be queen of the Chessmen army.
Stane’s attacks eventually force Tony to return back to some of his infamous bad habits, and he falls much further than he did the first time around -- he loses his company, gives up his armor to Rhodey, and ends up wandering the streets. It’s only when Stane pushes Stark after he’s trying to rebuild his life that Stark even comes close to getting revenge.
The Mandarin isn’t just a threat to Tony Stark, he’s a threat to humanity. Mandarin became a terror of the underworld before finding his way onto a crash landed alien ship and taking out its pilots to attain his Ten Rings of Power. Each of the rings grants Mandarin a different ability, ranging from simple things like elemental blasts of fire, ice and electricity, to being able to control minds and alter states of matter.
With those powers, he’s threatened the government of China to look the other way when it comes to his criminal empire. Where most villains are content with small, petty goals -- Mandarin seems to be interested in nothing less than absolute domination of the world.