Despite being a selfless hero who saved the world more than once, Tony Stark has made mistakes that have caused those around him to pay the price. Some actions of Tony’s were deliberate, some unintentional but there were also times he was an unsuspecting victim of others’ projected insecurities.

While his cavalier and laid-back attitude is dangerous for a man in power, there is some reassurance in how Iron Man is humanized. Tony’s capability to both make and accept his mistakes portrays him in a light that is unique to superheroes, a step away from perfectionist traits.

Updated on June 22, 2023, by Daniela Gama:

Even after his (spoiler alert) death, Tony Stark remains one of the most beloved and memorable superheroes to date; the amount of times he is often mentioned in the franchise despite not being present anymore just proves the point. With new, exciting MCU projects coming to our small and big screens — including the gritty spy Disney+ series Secret Invasion — and fresh villainous faces presenting themselves to viewers, fans may find themselves looking back at some of the most frightening antagonists. Funnily enough, many of them were familiar with Stark.

10 Vision

Despite witnessing the turmoil of events over Ultron’s creation, Tony proves his cleverness in the MCU once again after wanting to upload his Artificial Intelligence J.A.R.V.I.S. into a synthetic body, creating Vision (Paul Bettany). While Vision is a creation of Tony, Bruce, and Helen Cho, Tony’s prompting to utilize the synthetic body is what led to his birth.

When Vision was revealed to have good intentions at heart, he declared that he would fight alongside the Avengers to protect humanity. However, his decision to create Vision could have just as easily been disastrous, ultimately providing Ultron with another ally.

9 Wanda & Pietro Maximoff

Both Wanda (Elizabeth Olsen) and Pietro Maximoff (Aaron Taylor-Johnson) are superhuman fraternal twins who are native to Sokovia. While both suffered the death of their parents in front of them at the hands of Stark Industries missiles, both twins grew to resent the Stark name.

While they joined Hydra and willingly underwent experimentation which enhanced their abilities, their passionate hatred and resentment towards Tony Stark and the United States military encouraged them to join hands with Ultron. Although they were able to see Ultron’s misguided ways, joining the Avengers, Stark’s prior involvement with military weapons affected many innocent lives including the Maximoff twins.

8 Justin Hammer

Justin Hammer (Sam Rockwell), who only appears in Iron Man 2, was an insensitive military contractor of Hammer Industries and a rival of Stark Industries. As a rival competitor who wanted to improve his standing, he attempted to discredit Tony by recreating the Iron Man suit.

In frustration over his failure to succeed and anguish over his humiliation and being repeatedly overshadowed by Stark, he desperately recruits Ivan Vanko (Mickey Rourke) and both join forces to destroy Tony’s legacy and undermine Stark Industries.

7 Aldrich Killian

Killian (Guy Pearce) was an arrogant, conceited, yet passionate ambassador of his research with enhanced soldiers. Growing up insecure over his physical disabilities, he tried his best to utilize his scientific intelligence to help him overcome his shortcomings.

When his idol Tony Stark didn’t show any interest in joining his research, he became bitter and resentful towards him. Tony’s decision to willfully ignore Killian led him to a moment of self-reflection where he embraced the anonymity of his presence, making him unpredictable in his future endeavors (and soon, an unlikable MCU villain).

6 Vulture

Adrian Toomes (Michael Keaton) donned the alias of Vulture when turning towards crime after losing the contract to clean up after the Battle of New York. He began to steal the Chitauri technology used in battle, refurbishing them into weapons that he could sell on the black market.

Although Tony Stark created Damage Control to clean up the mess, ultimately taking responsibility for the damage caused by an extraterrestrial attack, Toomes resented how this put his company out of business, affecting his long-term income and livelihood.

5 Iron Monger

Obadiah Stane (Jeff Bridges) was Howard Stark’s (John Slattery) business partner in Stark Industries. Although his actions mostly stemmed from his jealousy of Tony when he took over as CEO of Stark Industries, his power-hungry demeanor led him to enlist the powerful Ten Rings to kidnap and kill Tony.

However, Tony’s decision to fight back using weaponized armor and ultimately shift away from weapon production spurred him to attempt to create his own version of the Iron Man suit for military use. It’s fair to assume Obadiah Stane would be just as much of a cold-hearted businessman irrespective, but the question of whether he would go on a vicious rampage remains.

4 Ivan Vanko

Ivan Vanko was the son of a scientist who worked alongside Howard Stark until he was deported when he told the first arc reactor designs to the black market. Despite being considered one of the most poorly-written villains, Vanko spent much of his life resenting the Stark name, choosing to target Tony as he grew to prominence as Iron Man.

While Tony would have been targeted nonetheless, he slipped up due to his own egoistic perception that no one else can create what he achieved. Despite being considered one of the weakest villains in the MCU, Vanko targeted his public perception as a hero, by demonstrating Tony is not invincible.

3 Zemo

Baron Zemo (Daniel Bruhl) grew resentful towards the Avengers over the loss of his family in the Battle of Sokovia. Although they successfully took down Ultron, Zemo was disgruntled with the absence of acknowledgment of the innocent lives that were lost, splitting the Avengers by creating an internal conflict.

Instead of being held accountable for their actions which spurred the Battle of Sokovia, the Avengers were deemed heroes. As Ultron was the result of Tony’s attempt to put a suit of armor around the world, the death of Zemo’s family and his consequent actions were all the result of Tony’s misguided decision.

2 Mysterio

Quentin Beck (Jake Gyllenhaal) originally worked for Stark Industries, developing holographic technology, first introduced in Captain America: Civil War. It is revealed that Beck became aggravated when Stark renamed his life’s work B.A.R.F (Binarily Augmented Retro-Framing).

As Beck reveals Tony fired him, calling him unstable, there are questions raised about whether Beck’s version of what events transpired is true. Irrespective, his intent to become the next Iron Man was rooted in being discredited despite his hard work.

1 Ultron

Ultron (voiced by James Spader) was Artificial Intelligence created by both Tony Stark and Bruce Banner initially intended for the Peacekeeping Program. However, upon entering consciousness, Ultron deemed humankind to be the greatest threat to peace.

Although Tony’s actions to create Ultron stemmed from fear of another extraterrestrial attack that could threaten humankind, his actions caused a much greater threat to all of humanity. While the Avengers were successfully able to stop Ultron, there was a lot of collateral damage to even more innocent lives lost in the Battle of Sokovia. He was also (arguably) one of the most memorable MCU villains and deserved a second chance.

NEXT: Every MCU Villain Ranked From Worst to Best