While his rogue's gallery is nowhere near as big as some other superheroes, Iron Man has some very interesting and powerful enemies. While most of his enemies have an armored visage, there are others that venture somewhat out of that arena, although most are based at least partially in the arena of technological advances.
While Iron Man was the first superhero in the Marvel Cinematic Universe, his villains in the movies have mostly been overshadowed by other heroes in the franchise, such as Thor, who has had amazing villains in Loki and Hela, as well as Thanos, who was an enemy of The Avengers and not just Tony Stark. However, Iron Man has some truly evil villains and here are 10 of the worst.
10 10. CRIMSON DYNAMO
Crimson Dynamo was one of Iron Man's earliest villains. In the '60s, Iron Man was involved in a lot of political stories centered on the post-WWII cold war era and Crimson Dynamo was there with Black Widow to put the American Iron Man against his Soviet counterparts.
Crimson Dynamo was Anton Vanko, one of the top Russian inventors of that era -- basically the Soviet version of Tony Stark. After Vanko's death, other men took on the role, with 11 different people wearing the Crimson Dynamo armor over the years. Arguably, the best version of the Iron Man villain was Alexander Nevsky, who held the role for over five years.
9 9. SPYMASTER
Spymaster is an Iron Man villain that first showed up in 1971 as an espionage specialist who infiltrated Stark Industries on more than one occasion. This version of the villain was just about a flawless thief and was able to team up with Justin Hammer at one point to take control of Iron Man's armor and caused him to destroy parts of the city.
Spymaster disappeared for years when the world thought he had died, but he was just lying low and biding his time. There were a few people along the way who took over his role but he didn't return until the Dark Reign storyline and played a major role in the Infinity: Heist story in 2014.
8 8. JUSTIN HAMMER
Justin Hammer was the villain in the movie Iron Man 2, the arms dealer who was a direct competitor to Tony Stark. In the movie, he stole Stark's technology and then created his own army of armed warriors that he planned to sell to the United States government -- although he was betrayed by Whiplash.
In the comics, he was a similar Iron Man villain, a rival of Tony Stark who caused more problems than almost anyone. Unlike the movie, Hammer was an older man in the comics, a billionaire financing and arming villains and criminals. He also worked with the Hand and Hydra and was a truly evil villain.
7 7. GHOST
Marvel Cinematic Universe fans met an interesting version of Ghost in the movie Ant-Man & The Wasp. That was a tragic character who was as dangerous as she was cunning. However, that character only really shares the name and powers of the Ghost from the comics but is nothing like that Marvel character under the mask.
In the comics, Ghost is an Iron Man villain -- a man who was once a data engineer who ended up infused with the ghost technology he created to become a corporate saboteur. He became an Iron Man villain when he was hired to infiltrate Stark Industries and over the years, worked for everyone from Justin Hammer to A.I.M.
6 6. WHIPLASH
Whiplash was the main antagonist in Iron Man 2, Mickey Rourke portraying Ivan Vanko, the son of a Soviet physicist who Howard Stark ruined in the past. As a result, Ivan wanted revenge against Howard's son Tony and created his energy whips to attack and try to kill Iron Man on more than one occasion.
Much like almost all Iron Man's comic book villains who made their way to the movies, Whiplash was changed. In the comics, he was Marco Scarlotti, a man who worked for a crime syndicate called the Maggia and was sent to battle Iron Man. Much like the movie, he had the cybernetic whips that he used as weapons and was a key Iron Man villain for over 30 years.
5 5. COUNT NEFARIA
Luchino Nefaria is one of the most powerful villains that Iron Man had ever faced, and even though he started out as an Avengers villain, he soon became known for his rivalry with Tony Stark. This is mostly because Tony developed a relationship with Whitney Frost -- the daughter of Count Nefaria -- which made their battle always so personal.
Count Nefaria was so powerful that he could battle The Avengers or The X-Men and remain on even ground with an entire team, which meant that Marvel needed to add the personal touch to make him battling one man make any sense, and they succeeded with Iron Man.
4 4. MADAME MASQUE
As mentioned, the reason that Iron Man and Count Nefaria's battles were so heated was that Tony Stark and Nefaria's daughter Whitney Frost were close. As fans of the comics know, Whitney is none other than Madame Masque, and the fact that Iron Man was a hero and Madame Masque was a villain made their relationship under their secret identities so awkward.
It also made their role as enemies very personal. For a while, the two were romantically involved and worked together until their relationship ended and both moved on. No longer dating, Madame Masque went back to villainy when her father died and she blamed Iron Man -- making her one of his most lethal antagonists.
3 3. OBADIAH STANE
Obadiah Stane was the villain from the first Iron Man movie, with Jeff Daniels playing him perfectly. He was also a very nuanced villain, someone who saw Tony Stark destroying everything he had helped Howard Stark to build and was fighting to keep hold of the company he was losing his grasp on.
With that said, Stane was also Iron Monger in the comic books and was responsible for possibly the most profound moment of Tony Stark's life -- the Demon in a Bottle storyline. When Stane took over Stark Industries and pushed Tony out, Iron Man fell to alcoholism and ended up homeless for a time. It was the most famous Iron Man storyline and Stane was the villain responsible for his downfall.
2 2. NORMAN OSBORN
Norman Osborn started out as strictly a Spider-Man villain as the Green Goblin. In those books, he was a good man in the start but slowly went insane due to the formula he used to gain his powers. However, it was not the Green Goblin who was one of Tony Stark's greatest villains -- it was Norman Osborn, whose Oscorp was a successful corporation on the level of Stark Industries.
When Norman ended up as a national hero after the Secret Invasion storyline, he was able to push Tony Stark out of his position of power with S.H.I.E.L.D. and started his own Dark Avengers team, with Norman as the Iron Patriot. He turned Iron Man into a villain the public's eyes and had more power than Tony ever did -- at least for a short time.
1 1. MANDARIN
When looking at Iron Man's villains, the one that sits at the top of the list is Mandarin. Forget about the character from Iron Man 3, which was a great character itself, albeit a red herring to the real villains of A.I.M. Instead, Mandarin from the comics was the polar opposite of Tony Stark.
While Iron Man developed his armor through his scientific know-how and genius, Mandarin found ten small cylinders on a crashed alien spacecraft and turned those into rings that gave him immense powers. While Iron Man touted technology, Mandarin claimed mystical energy and the two men's battles raged through the pages of Iron Man comics for over 50 years.