Tony Stark is one of the smartest people in the Marvel Universe. In addition to running several successful companies, inventing the Iron Man armor, and hanging out with people like Reed Richards, Tony has also saved the world countless times, both by himself and alongside the Avengers.

In doing so, he’s come up against villains and threats of all kinds, from marauding armies of space aliens to a giant dragon named Fin Fang Foom, that really seems to have it out for him for some reason. Often Tony comes out on top of these conflicts not due solely to the power of his battlesuit, but rather his intellect and ability to construct complex solutions on the fly. However, every now and then he comes up against a villain who is on his level intellectually; someone able to out-think or outplay him, at least for a time.

While Tony usually ends up coming out on top against these evil geniuses eventually, this list includes enemies that managed to catch him off-guard, or outmaneuver him into an extremely unfavorable position.

Here are the 15 Villains Who Outsmarted Iron Man.

15. Doctor Octopus

10 Doctor Octopus before switching bodies with Spider Man Iron Man: 15 Villains Who Outsmarted Tony Stark

Tony Stark considers Dr. Otto Octavius to be “small potatoes,” a local Spider-Man villain who is beneath him and his intellect. This is infuriating to Otto, and in the “Fix Me” arc from Matt Fraction’s Invincible Iron Man, he decides to bring the arrogant Avenger down a peg or two. Dying and encased in complex suit, moving only with the aid of his robotic octopus legs, Octopus kidnaps Stark and demands that he “fix” him, or else a nuclear bomb would be detonated in a densely populated area.

Of course, Otto doesn’t really expect Tony to be able to cure him, but after a lifetime of living in the man’s shadow, he wants to make him admit that he’s not as smart as he thinks he is. Tony manages to stop the bomb from going off, but fails to cure Otto’s illness, allowing Ock the smug satisfaction of going to his death with the knowledge that he “won.”

14. The Mandarin

Mandarin Iron Man: 15 Villains Who Outsmarted Tony Stark

Iron Man’s most fearsome and persistent enemy, The Mandarin is a brilliant scientist and martial artist, though he derives most of his power from the set of ten alien rings that he wears on his fingers, each of which bestows him with a different ability. The problem with powerful jewelry, however, is that it can be removed, and The Mandarin has been separated from his rings on more than one occasion.

When this happens, he is usually desperate to get them back– even going so far as to return to site of the original crashed alien ship where he found them, and using its advanced technology to construct a headband that allowed him not only to find his rings, but to transfer his consciousness into another body when his own was damaged beyond repair. He managed to evade Iron Man for a time by doing this, though he re-sculpted his new bodies to look just like him – only younger – because that’s just the kind of guy he is.

13. Obadiah Stane

Obadiah Stane Marvel Iron Man comics Iron Man: 15 Villains Who Outsmarted Tony Stark

A meticulous strategist and devoted player of chess, Obadiah Stane lives his life in the same way that he maneuvers the pieces on a chessboard. He even names his army of hired goons The Chessmen, because they are exact in how they carry out their orders. As the president of his own company, Stane International, Obadiah decides it isn’t enough, and goes after Stark Enterprises as well.

With a series of coordinated attacks on Stark businessess, and such underhanded moves as sending one of his agents undercover as Stark’s new lover, Obadiah pushes Tony back into alcoholism, and out of his company completely, forcing him to live as a vagrant on the streets. While Tony eventually got back on his feet, Stane’s victory over Tony looked for a time to be total and absolute.

12. The Beyonders

beyonders Iron Man: 15 Villains Who Outsmarted Tony Stark

An enigmatic and reality-warping race from a higher dimension, the Beyonders operate at a level beyond not only Tony Stark, but also nearly every hero or villain in the Marvel Universe. Able to easily handle powerful cosmic entities like The Celestials, The Living Tribunal, and the High Evolutionary, The Beyonders would likely consider Tony Stark nothing but an insect.

During a vast experiment involving the end of the entire multiverse, the Beyonders were found to be causing “incursions” – collisions of one universe into another – until eventually nothing at all would be left of the multiverse. Alongside many of the Marvel Universe’s greatest geniuses, Iron Man completely failed to halt these incursions, a task that was only accomplished by Doctor Doom, whom Stark would no doubt consider to be his intellectual inferior.

11. Doctor Doom

Doctor Doom Stan Lee Interview Iron Man: 15 Villains Who Outsmarted Tony Stark

Despite the fact that Tony Stark would consider himself smarter than Victor Von Doom, that fact is debatable, and certainly something that Doom himself would take issue with. In addition to saving the entire multiverse from the Beyonders when no one else, including Tony, could find a way to do so, Doom has now effectively taken Tony’s place as Iron Man.

After having his face fixed during the events of Secret Wars, Doom began pestering Tony with his attempts to turn over a new leaf, showing up on a number of his adventures despite Stark’s firm protestations. Now that Tony is in a coma as a result of the events of Civil War II, Doom has taken on the mantle of the Infamous Iron Man, dispensing his own brand of justice through an Iron Man suit. Stark would certainly find this to be the ultimate indignity.

10. Grey Gargoyle

Grey Gargoyle Iron Man: 15 Villains Who Outsmarted Tony Stark

A French chemist who accidentally turned himself into stone in a lab experiment, and was subsequently cursed with the ability to turn others to stone as well, The Grey Gargoyle is smart, but certainly not a genius.  As much a brute-strength-oriented villain as he was a scientist before his accident, the Gargoyle’s primary strategies are “turn people into stone” and “punch things.” He did once try to sell people he’d turned into stone as art pieces, but was promptly stopped by Iron Man.

During the events of Marvel’s Fear Itself, however, Grey Gargoyle was possessed by an ancient Asgardian hammer and faced Iron Man in Paris with a vastly increased power-set. Less of an intellectual victory and more of a moral one, the Gargoyle tricks Iron Man into destroying several stone citizens of Paris, before disabling his armor and forcing him to flee.

9. Ultron

Ultron Iron Man: 15 Villains Who Outsmarted Tony Stark

Built by Hank Pym, Ultron achieved sentience and turned against his creator, going on to plague the Avengers over and over throughout the years. A machine intelligence, Ultron is as smart as anyone one on Earth, though his intelligence can often be clouded by his anger towards the Avengers, and his desire to come out on top. As a result he’s worn a number of faces and mechanical bodies over the years, including taking over Stark technology on more than one occasion.

During Brian Michael Bendis’s run on Mighty Avengers, he took the form of his “Mother,” Janet Van Dyne, aka The Wasp. He did so by sneaking his programming into Iron Man’s armor, which was at the time fused with his body by the Extremis virus, and reshaping steel and flesh into her image. Totally helpless to do anything about it, Tony was saved by the rest of his team, after having what was presumably a really weird day.

8. Norman Osborn

Norman Osborn as Iron Patriot with Ant Man Iron Man: 15 Villains Who Outsmarted Tony Stark

Taking over S.H.I.E.L.D. at the end of Civil War, Tony Stark showed some pity to the supposedly reformed Norman Osborn, taking him at his word that his past as the villainous Green Goblin was behind him. Tony put him in charge of the Thunderbolts unit, forcing other villains to help capture unregistered heroes. When Osborn ended up saving the day from a Skrull Invasion at the end of Secret Invasion, he obtained even more power, taking over H.A.M.M.M.E.R., a S.H.I.E.L.D.-like military organization, and forcing Tony on the run.

Knowing that Osborn was after the secrets in his head, Stark was forced to start deleting his memories, using less and less complicated Iron Man armors as he lost his intelligence. By the time he faced Osborn in battle, he was wearing his original, obsolete armor against Norman’s advanced Iron Patriot suit. Despite the fact that he managed to keep his secrets out of Osborn’s hands, he was still reduced to a shell of his former self.

7. Ezekiel Stane

Ezekiel Stane Iron Man: 15 Villains Who Outsmarted Tony Stark

The son of Obadiah Stane, Ezekiel has been honing his intellect in order to take down Tony Stark since the age of nine, with his fingers in every corner of the global techno-terrorist movement. Believing Iron Man-style suits to be a waste of time, Ezekiel has focused his attention on modifying the human body itself, building lasers into his fingertips, along with a vast assortment of other weaponry and tech.

A truly modern threat, Ezekiel shocks Tony with his brutality, staging an attack on Stark’s companies using biologically modified suicide soldiers. While he never forces Tony into homelessness like his father did, he differentiates himself from Obadiah by surviving his encounter with Tony, and allying himself with the Mandarin, who he equips with his superior technology.

6. Recorder 451

Recorder 451 Iron Man: 15 Villains Who Outsmarted Tony Stark

An old Recorder robot built by the Rigellian race, Recorder 451 experienced a glitch that ensured he remembered everything he was ordered to record. After a lifetime of observation, he decided it wasn’t enough, and was driven to act. Seemingly an ally to to Tony, he helps him escape from the Voldi race, but was actually manipulating him into creating an opening for him to steal one of their sacred artifacts, the Heart of the Voldi, which led to their doom.

Furious at 451 for deceiving him, Stark found out that the rogue robot had actually been tricking Starks since before Tony was born. Recorder 451 struck a deal with Howard and Maria stark to help save them from an alien invasion, if he could make modifications to their unborn child. This all turned out to be a trick to get Tony to pilot a massive suit of armor called the Godkiller. Because nothing bad ever came from building something called a “Godkiller.”

5. His Own Armor

ironman sentient Iron Man: 15 Villains Who Outsmarted Tony Stark

Tony’s Renaissance Armor was the most advanced he’d ever built, which is really saying something. It contained not only weapons systems, but a completely self-contained life support unit that allowed him to shut himself off from the world. While he eventually realized this was bad for his health, it was too late, as the armor had achieved sentience, and considered itself the true Iron Man.

After attempting to turn his family and friends against him so that Tony would merge with the suit and be Iron Man full-time, the sentient armor gave up on him, stranding him on a desert island. Tony laid traps for the suit, and put up a good fight, but was ultimately no match for his creation. He survived only because he experience a heart attack, causing the suit’s latent programming to kick in and destroy itself to save its creator’s life. Later, the suit was rebuilt as a new body for Ultron, because of course it was.

4. The Kree Supreme Intelligence

Kree Supreme Intelligence Iron Man: 15 Villains Who Outsmarted Tony Stark

The Kree Supreme Intelligence is incredibly smart, which may have been apparent from its name.  Millions of years old, the Supreme Intelligence is a collection of knowledge culled from all of the greatest minds in the Kree Empire; a being capable of out-thinking any human. Despite looking like a giant green head in a jar, the Supreme Intelligence has died and returned multiple times, always managing to evade the heroes of Earth no matter how many times they defeat it.

After one of those apparent deaths, the Supreme Intelligence gathered a group of Kree rebels called the Lunatic Legion to help take over the moon.  You would think it could have come with a better name using its infinite knowledge, but who are we to judge.

While the Intelligence’s plans for revenge on Earth failed to pay off, it did end up ruining Tony’s plans for his business by providing one of his rivals with Kree technology, which has got to count for something.

3. Ultimate Black Widow

Black Widow v Iron Man Iron Man: 15 Villains Who Outsmarted Tony Stark

Tony Stark has always had a weakness for beautiful women in any corner of the multiverse, and it was almost the downfall of the Ultimate Universe version of Iron Man. Both members of The Ultimates, Tony and this version of Black Widow struck up a relationship, and even got engaged.  Tony was so smitten that he built her her very own suit of armor as a wedding gift.

Little did he know she was a traitor, working for the Liberators to destabilize America in an act of revenge for slights against her home country of Russia. Her plan took a number of Ultimates off the board, framing Captain America and Thor, killing Hawkeye’s family, and making it clearer than ever that Tony needs to be more careful about who he dates.

2. A Tony Stark LMD (Life Model Decoy)

Iron Man Tony Stark Demon in a Bottle Iron Man: 15 Villains Who Outsmarted Tony Stark

Life Model Decoys have saved a number of heroes in the Marvel Universe, but have also regularly revealed themselves to be far more trouble than they’re worth. After using an LMD to trick the Mandarin into believing that Iron Man was someone else, an attack on Stark Industries reactivated it, and it (of course) achieved sentience as a result.

The Life Model Decoy was in a perfect position to steal Tony’s identity, considering that it looked exactly like him. It wasted no time doing so, changing his signature and fingerprints. With the world convinced that the real Tony was an imposter, the LMD ran Stark Industries for a short time, even going on adventures with the Avengers.

Tony was eventually able to regain his identity, but the embarrassment of being replaced by a robot surely lingered.

1. Alcoholism (With Help From Odin)

Iron Man and Odin Iron Man: 15 Villains Who Outsmarted Tony Stark

Okay, so maybe this isn’t a villain per se, but Tony Stark’s nemesis throughout his life and career as an inventor and superhero has surely been his addiction to booze. Alcoholism doesn’t care how smart you are, and his intellect has done nothing to make him less susceptible to the pull of his drinking problem. A supervillain can be outsmarted, but an addiction must be faced head-on.

While Tony has been a dedicated member of AA, and has kicked his addiction, he’s relapsed on more than one occasion. In addition to the time that Obadiah Stane pushed him back into the arms of booze, he once willingly relapsed in order to save the world.

During the events of Fear Itself, he sought the All-Father Odin’s help against Odin’s evil brother’s attempt to conquer the world. Knowing that gods love it when you sacrifice things to them, he sacrificed his sobriety, wrestling with his fall off the wagon even after humanity was safe.

Are there any other villains who outsmarted Iron Man? Let us know in the comments!

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