As the former headlining hero of the Marvel Cinematic Universe, Iron Man has become one of Marvel Comics' most popular characters. A weapons dealer created in 1963 by Stan Lee and Jack Kirby, Tony Stark was made to challenge readers into identifying with a hero they would ordinarily despise.

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Through heroic sacrifice and character growth, Iron Man has become a popular figure with crowds both real and imaginary. That said, Iron Man still has plenty of detractors. Whether crime lords, business rivals, or the bearer of a passed-around metahuman identity with Stark-emblazoned baggage, the Golden Avenger has almost as many enemies as suits of armor.

10 Whiplash Has Repeatedly Struck At Iron Man

Mark Scarlotti as Whiplash lunges forward

Whiplash is one of many in a line of disgruntled Stark Industries employees who have taken up arms against their former boss. Mark Scarlotti was an electrician who invented a high-tech whip, using it to battle Iron Man on behalf of the Maggia, Marvel's mafia stand-in.

Scarlotti was later diagnosed as manic depressive and attempted to go straight, though he was killed. Several others have taken up the Whiplash identity since, most notably Anton Vanko. After witnessing someone using a stolen Iron Man armor destroy his Russian village and kill his father, Vanko swore vengeance on the Golden Avenger.

9 Spymaster Is An Evil Expert Of Espionage

Spymaster holds a pistol

Like Whiplash, Spymaster is another identity that has been passed from one crook to another. While the identity of the original Spymaster was never revealed, Nathan Lemon and Sinclair Abbott are the names of the second and third to use the name. Never a wielder of superpowers, Spymaster is a savant in combat, tactics, and espionage.

Each Spymaster is devious for different reasons. The third Spymaster sought to prove himself a true supervillain and was responsible for the death of Happy Hogan. The second discovered Iron Man's secret identity and severely beat him. Most notably, the original Spymaster successfully stole Stark's Iron Man blueprints and sold them to Justin Hammer.

8 Kang Caused Iron Man To Betray His Teammates And Readers

An image of Kang The Conqueror striking with his sword

In addition to being one of Marvel's most confusing characters, Kang the Conqueror is one of Iron Man and the Avengers' deadliest enemies. A time-traveling despot with a thirst for conquest, Kang has used his future tech and armies to wreak havoc on the present day of the Marvel universe.

Though Kang holds animosity for all the Avengers, he has special hatred for Iron Man. Part of this is because of Stark's aptitude for technology, but Stark's refusal to accept Kang's future as superior also frustrates him. Kang once brainwashed Iron Man into betraying the Avengers; so devious was this act that it became known as one of the worst Iron Man stories of all time.

7 The Crimson Dynamo Is Stained With The Blood Of Its Wearers

Crimson Dynamo in Marvel Comics

There have been 13 wearers of the Crimson Dynamo armor in Marvel Comics history. Though most have not been outright villains, many have been allied with the Russian government, advocates of Stalinism, or both. This has often led them into conflict with Iron Man and Stark, whom many have viewed as a weapon of capitalism.

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The first Crimson Dynamo armor was created by Anton Vanko (no relation to Whiplash), who sought to prove his government's power against the American Iron Man. Since then, the identity and armor of the Crimson Dynamo has frequently been employed by K.G.B. associates, though many have turned sympathetic and met tragic ends.

6 Iron Monger Sought To Prove Himself Stronger Than Stark

Obadiah Stane as Iron Monger 80s Comics

Obadiah Stane was brought to life by Jeff Bridges in 2008's Iron Man. A devious businessman who exploits his opponents' psychological weaknesses, Stane became the Iron Monger after discovering Stark's notes on the Iron Man armor. Stane would use his armor to best Iron Man in combat several times.

Stane also bought Stark's company out from under him, driving him to alcoholism again. Though Stark eventually recovered and beat the Iron Monger, Stane's scion, Zeke, would also menace the Armored Avenger. Zeke followed in his father's financial footsteps, using the family business and cybernetic enhancements to battle Tony Stark.

5 Madame Masque And Iron Man's Relationship Ended In Heartbreak

Madame Masque holds a golden gun in Marvel Comics

Whitney Frost's father Count Nefaria is a devilish Iron Man villain in his own right, but Frost has proven a far larger threat. After her father trained her in combat, tactics, and leadership, Nefaria handed over to her the reigns of the Maggia. Frost took on the identity of Madame Masque after a failed raid on Stark Industries scarred her face.

Madame Masque and Tony Stark were once romantically involved, but Masque's struggles with paranoia led to her turning on Iron Man. Since then, Whitney Frost has organized armies of supervillains, blackmailed Avengers, and stole Stark Industries secrets to get at her former lover.

4 Justin Hammer Gives New Meaning To "Ruthless Businessman"

Justin Hammer and Tony Stark argue

Justin Hammer is one of Tony Stark's most dedicated enemies, but Hammer has never taken up arms against Stark himself. Instead, the aged billionaire has sought to bring Stark to ruin by equipping armored underlings and attempting hostile takeovers.

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Justin Hammer is largely responsible for the proliferation of supertech in Marvel's villain community. Hammer also once took over the Iron Man armor and used it to kill an ambassador, framing Stark. Hammer additionally caused the Armor Wars, an event in which Iron Man was forced to fight a number of villains to whom Hammer had sold StarkTech armor in exchange for profits.

3 Norman Osborn Became The Iron Menace

Norman Osborn as Iron Patriot in Marvel Comics

Though Norman Osborn is best known as Spider-Man villain Green Goblin, Osborn firmly positioned himself as the anti-Tony Stark in the Dark Reign storyline. Following the Skrull invasion of Earth, Osborn installed himself as director of the S.H.I.E.L.D.-like H.A.M.M.E.R. and new leader of the Avengers.

As leader of the Avengers and H.A.M.M.E.R. director, Osborn had access to all of Stark's resources, including his armor. Osborn sought to undermine Stark's work as the former Director of S.H.I.E.L.D. and used the Dark Avengers to hunt superheroes. Osborn also stole an Iron Man armor, dubbed himself the Iron Patriot, and mercilessly beat a brain-damaged Tony Stark.

2 The Mandarin Is Iron Man's Equal

The Mandarin in Marvel Comics puts forward a fist wearing the Ten Rings

An honorable genius with dreams of world-conquering, the Mandarin has ever been the most equal of Iron Man's enemies. His real name unknown, the Mandarin first created the Ten Rings from the technology of a long-dead alien dragon. In his first major attempt at conquest, the Mandarin captured Tony Stark, leading to Stark's creation of the Iron Man armor.

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The Mandarin has since held a grudge for Iron Man, but he has never lost sight of his original goal: global domination. To this end, he has allied himself with aliens and Asgardians, battled the Avengers, and aided in the Hydra takeover of America.

1 Iron Man Can Never Defeat Himself

Tony Stark looks at his Iron Man helmet in Demon in a Bottle by Marvel Comics

For some heroes, their greatest foe is someone who rejects their values; for others, it is a person who has done the hero a great wrong. Tony Stark's greatest villain has done these things, but that greatest villain is Stark himself. His arrogance, his struggles with trust and alcohol, and his own capacity for invention have made Iron Man his own greatest enemy.

In Civil War, Iron Man was responsible for the passage of the Superhero Registration Act, inciting the conflict. Iron Man's refusal to trust the Avengers with his identity for years led to dozens of fights from the Silver Age to the Dark Age of comics, while his technology has enabled dozens of supervillains. A hero who has saved the world hundreds of times, Iron Man must still contend with himself.

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