In a universe filled with a wide array of superpowered beings, Iron Man is just a smart guy with lots of money. Like Batman, he relies on his technology and his wits to allow him to keep up with a wide variety of bad guys. Oftentimes, the battles Iron Man faces are fairly easy ones, although there are times when he finds that his greatest enemy is himself.
Sometimes, though, Iron Man has more trouble saving the day. These are the villains that Iron Man has the most trouble taking down, even when he’s got his full array of suits.
5. The Crimson Dynamo
A Cold War relic that still packs a major punch, the armor of the Crimson Dynamo has actually been worn by a number of different characters in the long history of Marvel Comics. In essence, though, the Crimson Dynamo is meant to be a Russian version of Iron Man, and the two battle as much over their differences in ideologies as they do over anything else.
Like many of Iron Man’s most memorable foes, the Crimson Dynamo weaponizes who Iron Man is, and turns those qualities against him.
4. Madame Masque
Tony Stark is as legendary in the bedroom as anywhere else, and Madame Masque may be one of his most high-profile lovers-turnedtenemies. As the head of a massive criminal organization, Madame Masque packs an incredible punch, and has used her considerable skill in both combat and espionage to wreak havoc on the Avengers — and on Tony specifically. Whether it’s stealing Stark Industries’ secrets or engaging in open battle, she’s a consistent thorn in Tony’s side.
3. Iron Monger
Everyone likely knows at least a little about Iron Monger, who was brought to life memorably by Jeff Bridges in the original Iron Man. Obadiah Stane attempts to exploit the technology that Tony Stark created to his own selfish ends.
Stane’s version of the armor proved powerful enough to defeat Tony in battle several times, and he’s also always buying Tony out from the company that bears his name. Whether it’s in battle or in the boardroom, Stane is an all-time great foe for Tony.
Kang and Tony seem fairly unlikely to cross paths in the movies, but in the comics he’s proved to be one of Iron Man’s fiercest foes. Kang is a time traveler with an enormous brain, so it’s only fitting that Tony’s smarts would bother him.
Kang also firmly believes that the future he’s attempting to build is the best possible option, but Tony refuses to see things that way. Kang and Tony have real, actual disagreements, which is part of what makes them such a fascinating pairing. Kang may be the more powerful, but he wants Tony to want to join him.
1. The Mandarin
The Mandarin is designed as Tony’s equal, and that is what has often made him so difficult for him to handle. In the comics, it’s the Mandarin who originally captures Tony and forces him to build the suit, and he’s resented the weapons magnate ever since.
The Mandarin’s ultimate goal is world domination, though, which is why he’s aligned himself with anyone he can in the hopes that they’ll be able to help him take down Iron Man once and for all. He’s gotten close, but thankfully he hasn’t succeeded just yet.
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