By Marc Strom

If you measure a hero by the quality of their villains, then Iron Man stands an armored head above the rest!

When "Iron Man" hits the big screen on May 2, ol' Shellhead goes toe-to-toe with the menace of Obadiah Stane, aka the Iron Monger, in a slugfest for the record books! But while Stane calls himself one of Tony Stark's greatest enemies, we've sifted through the annals of Iron Man's past to compile a list of rogues just as notorious, from the Mandarin to Fin Fang Foom and everyone in between!
Iron Monger/Obadiah Stane
Corporate CEO Obadiah Stane gave Tony Stark one of his most crushing defeats when he succeeded in wresting control of Stark International from the Armored Avenger. Renaming the company Stane International, Obadiah began constructing an armor of his own based on Stark's notes. When Tony managed to lift himself out of the hole he'd fallen in, Stane donned his battlesuit, becoming Iron Monger in the hopes of defeating Iron Man. After his own defeat, however, Stane committed suicide rather than face justice for his actions.

The Mandarin
Once a prominent member of the Chinese government, the Mandarin fell from power with the rise of the Communist Party. Forced to aimlessly wander the country, he stumbled across a ruined spaceship and discovered 10 rings in the vessel, each of capable of producing great power. Eventually mastering the rings, the Mandarin set to work trying to regain the status he had lost. Unfortunately for him, such plans have never reached fruition as Iron Man has consistently stood between the would-be tyrant and victory.

Justin Hammer
An industrialist with questionable ethics—to say the least—Justin Hammer once managed to frame Iron Man for the murder of a United Nations ambassador. In his quest to redeem his name and prove his innocence, Shellhead discovered Hammer had funded various super villains with his company's money and shut his operation down. Over the years the two have clashed on numerous occasions, including during the first "Armor Wars" when Hammer stole Stark's technological secrets and sold them to the high-tech villains of the Marvel Universe.

Madame Masque
A one-time lover of Tony Stark's, the deadly Madame Masque sits at the head of one of the most powerful families in the the crime organization known as the Maggia. The daughter of super villain Count Nefaria, who trained her as one of the world's premiere criminals, Whitney Frost's long and complicated history with the Golden Avenger makes her one of Iron Man's most unique adversaries. Though Madame Masque does not possess any super human powers, the resources at her disposal allow her to cause more than enough trouble for Shellhead.

Crimson Dynamo
The first man to possess the title of the Crimson Dynamo, Professor Anton Vanko, also invented the suit of armor capable of controlling and utilizing electricity in all its forms. In his first mission against Iron Man, Vanko defected from the Soviet Union and became an ally of Tony Stark's. Some time later, when Vanko's superiors in the USSR sent the second Crimson Dynamo and the Black Widow after Vanko, the professor sacrificed himself to save Stark's life.

Titanium Man
Creating a suit of titanium modeled after Iron Man's own suit, Boris Bullski challenged the Armored Avenger in front of worldwide television…only to face a crushing defeat before the cameras! Determined to redeem himself, Bullski repeatedly returned to plague Iron Man's life. Since his first appearance, several others have worn the Titanium Man armor, though the identity of the man—or woman—underneath the armor in his most recent appearances remains a mystery…

Whiplash
Mark Scarlotti never made the best decisions in his life. A brilliant child with a bright future ahead of him, he fell in with the wrong crowd and wound up creating high-tech weaponry for the Maggia. Eventually transforming himself into Whiplash, Mark encountered Iron Man in one of his first outings as a super villain. Faced with defeat after defeat at the hands of Shellhead, Scarlotti reinvented himself as Blacklash for a time. Back in his Whiplash identity, he eventually met his tragic end when the Iron Man armor gained sentience and rebelled against its creator.

Ultimo
Giant alien robot: 'Nuff said. Iron Man's arch-nemesis, the Mandarin, discovered the dormant Ultimo within a volcano, and after many failed attempts finally reawakened the millennia-old creation. Unstoppable and untiring, Ultimo lives up to his name as one of Shellhead's ultimate villains! After trapping Ultimo underneath the Earth's mantle, Iron Man thought he'd heard the last of the menace…until the robot returned, stronger and larger than ever, requiring Stark's best friend and confidante James Rhodes to assemble an Iron Legion of Tony's closest allies clad in his previous armors to stop the monstrosity once and for all!

Fin Fang Foom
Don't be fooled by his old school appearance—Fin Fang Foom ain't your daddy's dragon! An alien being stranded on Earth, Foom first came into conflict with Iron Man when the creature manipulated the Mandarin—him again!—into releasing him from his dormant state. Eventually discovering Foom's true intentions, the Mandarin teamed up with Iron Man and War Machine to prevent the alien and his brethren from taking over the Earth!