Across Iron Man's lengthy history in the Marvel Universe, the Armored Avenger has tangled with some of Marvel's most underrated powerhouse supervillains on his own. As Tony Stark has constantly upgraded his signature armor and its accompanying tech to stop them, Iron Man's longtime antagonists steadily become more deadly along with him, posing a threat to the whole world.

Now, we're taking a look back at some of Iron Man's most powerful villains, and what exactly makes them so formidable. While some of these bad guys have caused trouble all around the Marvel Universe, they all hold a special place in Iron Man's rogues gallery.

RELATED: Marvel Heralds Iron Man 2020's Imminent Arrival with Variant Cover Series

The Mandarin

The Mandarin

Created by Stan Lee and Don Heck in 1964's Tales of Suspense #50, the Mandarin is, in many ways, Tony Stark's polar opposite. Just as Tony had emerged from a cave as his best, true self in a suit of electromagnetic armor, the Mandarin had left a remote cave in China armed with ten rings of extraterrestrial origin each wielding its own incredible power.

Obtained from a crashed alien seeking refuge in the cave, the Mandarin slew the otherworldly visitor and used the rings to create his own criminal empire that rivaled Tony's corporate holdings. The Mandarin's ten rings can fire electricity, flame, concussive energy, disintegration beams, and polar ice as well as generate gravity fields, absorb light energy, control minds, create vortices, and rearrange matter, making the villain especially dangerous even without his martial arts training and vast resources. Although he's arguably Iron Man's most important historic foe, the real Mandarin won't make his full Marvel Cinematic Universe debut until Shang-Chi and the Legend of the Ten Rings.

Ultimo

An image of comic art depicting Ultimo under attack from fighter jets

Ultimo represents the advanced technological implications of Iron Man taken even further as a sentient robot designed to be the ultimate weapon. Thousands of years old and constructed by an extraterrestrial race, Ultimo completely eradicated his own creators and traveled the cosmos annihilating all in his way before crash-landing over a century ago on Earth where he lay dormant within a volcano in China.

RELATED: Slott's Ultron Agenda Pushes Tony Stark Towards a Dangerous Future

Created in 1966's Tales of Suspense #66 by Lee and Gene Colan, Ultimo was eventually discovered and reactivated by the Mandarin. He was now even more powerful after being charged from over a century by the geothermal energy within the volcano. Reprogrammed to serve the Mandarin, Ultimo is capable of unleashing devastating energy attacks, is housed within a nigh-indestructible alloy body, and possesses an adaptive defensive system, making him an especially difficult foe for Iron Man to defeat with each subsequent engagement.

Count Nefaria

Count Nefaria

Originally introduced as a villain for all of the Avengers in 1965's Avengers #13 by Lee and Heck, Count Nefaria would ally himself with several members of Iron Man's rogues gallery as part of his plan to extend his criminal empire around the world. A wealthy Italian aristocrat, Luchino Nefaria joined the Maggia crime family and initially singled out Iron Man for revenge after his first defeat at the hands of the Avengers.

Through experimentation by Baron Zemo, Nefaria gained the superpowers of the Living Laser, the villainous Power Man (not to confused for Luke Cage), and Whirlwind. As such, Nefaria can fire energy blasts while also possessing superhuman strength, speed and endurance to the point where he has fought Thor hand-to-hand to a standstill. As the father of Madame Masque, Nefaria and his daughter have plagued Iron Man for years, both on their own and with supervillain teams like the Lethal Legion.

Grey Gargoyle

Originally created by Lee and Jack Kirby in 1964's Journey into Mystery #107 as a villain for Thor, Paul Pierre Duval was a French chemist accidentally is exposed to chemical compound that turns anything to stone by touching it. Naturally, he became a supervillain named the Grey Gargoyle. After being defeated by Thor, the villain turns his attentions to Iron Man, targeting Stark Industries after becoming a corporate spy and industrial saboteur.

RELATED: The Best Iron Man Comics for New Readers

Grey Gargoyle and his formidable abilities would clash against Iron Man several times over the years, notably during the crossover event Fear Itself where he was empowered by Asgardian magic and transformed the entire population of Paris to stone. While he was eventually defeated by Iron Man, it took the Asgardian power of Odin to revert his victims back to normal.

Fin Fang Foom

Created by Lee and Kirby in 1961's Strange Tales #89, Fin Fang Foom was an extraterrestrial dragon that had laid dormant in China for millennia before being revived by the Mandarin to be used as part of scheme to take over one third of China. When Mandarin realized he was being manipulated, he joined forces with Iron Man and War Machine to defeat the dragon.

As the size of a kaiju, Fing Fang Foom possesses incredible destructive power, including a corrosive acid spit, accelerated healing factor, and super-speed. However, the dragon is also incredibly intelligent instead of a mindless beast, nearly outsmarting someone as smart as the Mandarin.

KEEP READING: Tony Stank: Iron Man Has His Own Cologne in the Marvel Universe