With his brilliant mind, nigh-bottomless checking account, higher-than-high-tech armored suits and irresistible facial hair, Tony Stark has never had any trouble finding women willing to spend time with him, in every sense that phrase implies. With the kinds of social circles he runs in—superheroic and international business — it is inevitable that many of the women he meets are at least as smart, resourceful and tough as he is, if not more so.
In this list, we take a look at the most powerful ladies Tony has been either lucky or unlucky enough to become entangled with. Some of them are physically strong enough to crush him like an old soda can, regardless of whether he’s wearing his famed armor. Others are master manipulators, skilled at exploiting Tony’s emotions and addictive personality for their own gain. And still others are just plain crazy enough to go to lengths Tony can’t see coming until it’s too late. But what they all have in common is that every single one has either given Iron Man a serious run for his money, or, if they haven’t, it’s only out of the goodness of their hearts and Tony should be grateful that they’re on his side.
15. NATASHA ROMANOV
Tony Stark first met the Black Widow in Tales of Suspense #52, though he was too busy wining and dining her alter ego, Natasha Romanov, to notice at first that she was a Soviet spy. While Natasha did find Tony attractive, she didn’t let that stop her from doing her job: eliminating a Russian defector, Vanko, who had recently found employment at Stark Industries.
While Black Widow keeps Tony distracted, her associate Boris attacks Vanko in his lab, but Vanko sacrifices himself to stop Boris from getting away. Tony can only watch as Vanko dies and Black Widow flees, down but definitely not out. She of course would return to Tony’s attention later on, first as a villain and later as an ally and as a good friend.
14. JENNIFER WALTERS
Jennifer Walters was an ordinary if timid lawyer until an emergency blood transfusion from her cousin, Bruce Banner, transformed her into the Sensational She-Hulk, one of the most physically intimidating heroes on the planet. She has joined several superhero teams over the years, most notably the Avengers and the Fantastic Four, and has also joined up with Tony Stark in a casual fling or two.
While She-Hulk sided with Iron Man and the other pro-registration heroes during the “Civil War” event, she did not approve of their treatment of the Hulk, whom Iron Man shot into space. She went after Tony and made her disapproval clear in extremely violent terms, throwing him around an airfield as if he weighed no more than a stuffed animal while berating him for acting like a dictator.
13. JANET VAN DYNE
The Wasp may have started out as the weak link of the Avengers, playing the role of damsel in distress at least as often as she played the role of hero, but she certainly didn’t stay that way. By the early ’80s, around the same time that she had a brief romantic relationship with Tony Stark, Jan was elected leader of the Avengers, a position previously held by the likes of Captain America, Thor and Iron Man himself. She led them long and well, definitively proving that her days as a helpless punching bag were over.
Aside from her numerous accomplishments as an Avenger, Janet has also had a successful career as a fashion designer, creating costumes for some of her teammates and especially for herself, demonstrating that she is as creative and hardworking as she is heroic.
12. SUNSET BAIN
Despite being an electronics genius in her own right, Sunset Bain decided she’d rather cheat her way to the top of the corporate world. When Tony was still in college, Sunset seduced him in order to wangle Stark Industries secrets out of him and set up her own business, Baintronics. The scheme worked, and as soon as she had what she wanted, Sunset dropped poor naive Tony like last year’s computer models.
Sunset’s company became a roaring success, but that was was just the beginning of her long and crooked career. As the alliteratively named Madame Menace, Sunset sells weaponry to supervillains, but there truly is no honor among thieves; Sunset has been known to betray her criminal allies as unflinchingly as she once betrayed Tony. The crooks are never happy about it, and some even try to exact revenge, but Sunset always rises again.
11. INDRIES MOOMJI
On her first day at Stark Industries, Indries Moomji fell victim to an attack by hypnotized Stark employees. When a concerned Tony Stark came to visit her in the hospital, he immediately fell in love with her. The feeling seemed to be mutual, and the two embarked on a long and passionate romance. But the relationship was just an illusion, as Moomji was working for Stark’s rival, Obadiah Stane, the entire time.
Her job was to get Tony so emotionally attached to her that the break-up, when combined with stress incurred by Stane’s other schemes, would drive him off the wagon. Sadly, the plan works exactly as they hoped; after resisting the lure of the bottle for several days, it is Indries’ unexpected cruelty that breaks him at last.
10. MARIA HILL
After having spent much of her career at S.H.I.E.L.D. as second-in-command to Nick Fury, Maria Hill got her chance to lead the organization when Fury was forced into hiding after the events of “Secret War.” As such, she had the power to make many a superhero’s life miserable during “Civil War” and she wasn’t shy about using that power, directing S.H.I.E.L.D. to pursue Captain America and every other rebel to the fullest extent possible.
Maria ended up losing the number one spot to Tony Stark, with whom she later embarked on a brief tryst. She even led the Avengers for a while before Captain America returned to take that job as well. Still, not many people can say they’ve headed two of the most powerful organizations on the planet but, for better or worse, Maria Hill can.
9. KATHY DARE
Despite not having any superpowers, Kathleen Dare is probably the most frightening woman Tony has ever dated. After meeting Tony at a charity event, she pursues him relentlessly, constantly inviting him or demanding to be invited for drinks or dinner. Whenever Tony tries to spend time with any other woman, Kathy either storms out in a rage or attacks the woman in question.
Tony ignores all of these warning signs, insisting to his friend Rhodey that he can leave her anytime he wants; less than a page later, Kathy suggests he spend less time with Rhodey because Rhodey doesn’t like her. When Tony does finally end their blatantly abusive relationship, Kathy shoots him, leaving him paralyzed. This being comics, he eventually recovers. Kathy does not fare quite so well. In Iron Man #286, she commits suicide while declaring her continuing love for Tony Stark.
8. BETHANY CABE
As one of the only positive examples on this list, Bethany Cabe was Tony Stark’s girlfriend during the famous “Demon in a Bottle” storyline, in which Iron Man’s struggle with alcoholism begins. She has a front-row seat to Tony’s decline and, while all of his other friends can’t or won’t help, steps up to the plate to make him see just how far he has fallen. When he finally does ask for help, she is the one who sees him through the tough days of withdrawal that follow.
While Bethany, a highly trained bodyguard who once knocked out Whiplash, probably could take down Tony Stark in unarmed combat, her true strength is in her compassion and her willingness to see her lover through some of the worst days of his life.
7. EMMA FROST
As one of the most skilled telepaths in the Marvel Universe, Emma Frost is certain to be more powerful than just about anyone she chooses to be with, and that includes Iron Man, with whom she admits to having an “arrangement” in Civil War #3. In addition to her mental abilities, Emma more recently gained the ability to turn her body into an organic diamond form that is almost indestructible.
Although she can’t use her telepathy while in diamond form, it does make her immune to extreme changes in temperature, as well as physical blows and energy blasts from even the most powerful of opponents. Pity the poor sap who think it’s a good idea to cross Emma Frost; the only thing uncertain about the outcome is whether she will choose to obliterate them mentally or physically.
6. JUSTINE HAMMER
The Hammer family has a long history of trying to get the best of both Tony Stark and his alter ego, Iron Man. Unscrupulous businessman Justin Hammer started the tradition, and his equally corrupt daughter Justine was more than happy to keep it going. In the main Marvel Universe, their relationship remains — or has so far remained — adversarial but platonic.
Over in the Ultimate Universe, where everything is darker and everyone is more bitter, Justine and Tony end up jumping into bed together, after Justine threatened to murder him several issues earlier. That wasn’t an idle threat, either, since her father’s experiments have granted her superpowers. What she fails to mention until after they get physical, however, is that she has been working for Tony’s insane grandfather the entire time. Well, nobody’s perfect.
5. MARIANNE RODGERS
Tony and Marianne were together for only a short while before they realized she had telepathic and ESP abilities. Unfortunately, these powers proved too much for her to handle. She suffered vivid, frightening hallucinations and ultimately lost touch with reality, prompting Tony to commit her to a mental hospital and end their relationship.
Furious with Tony abandoning her, Marianne leaves the hospital with vengeance on her mind, determined to track down her ex and murder him. But while Marianne certainly has the raw power to destroy Iron Man, her emotional vulnerability proves her undoing. She unleashes a bolt of devastating mental energy at Iron Man and misses, instead hitting the villain Midas and rendering him brain-dead. Marianne then collapses and is returned to the hospital.
4. WHITNEY FROST
Upon learning she is the biological daughter of infamous crime lord Count Nefaria, Whitney Frost takes over his organization, the Maggia. As Big M, she begins a long, involved plot to steal Stark Industries secrets by seducing Tony’s S.H.I.E.L.D.-issued bodyguard, Jasper Sitwell. But the men under her command show little respect for their female leader and often threaten to overthrow her, forcing Whitney to become increasingly ruthless both with them and in her criminal schemes just to protect her position at the top.
After failing to secure the desired Stark tech and suffering facial disfigurement in a plane crash, Whitney takes to wearing a gold mask and rebrands herself as Madame Masque. But Tony only cares about the glimpses of humanity he has seen in her and happily pursues a relationship.
3. MAYA HANSEN
Iron Man 3 starts with a flashback to a one-night stand Tony Stark once had with a woman named Maya Hansen. Maya is a brilliant scientist in her own right; she is the creator of the Extremis virus, which she intended to use to help people recover from serious injuries. But after being jilted by Tony, Maya allows her emotions to override logic. She gives her research on Extremis to Advanced Idea Mechanics, a less-than-scrupulous scientific organization, who naturally use it for less-than-scrupulous purposes.
Maya ultimately has a change of heart and tries to help Tony stop mad scientist Aldrich Killian, even going so far as to threaten to kill herself in a bid to convince Killian to release Tony, who he kidnapped earlier. Maya does end up losing her life, but not in the way she intended: Killian shoots her before she can shoot herself.
2. ROXANNE GILBERT
Although Iron Man only dated her for a short while, Roxanne Gilbert quickly established herself as one of the most strong-willed paramours he’d had up until that time. In her first appearance in Iron Man #59, Roxanne stands up to her supervillain brother, Firebrand, and gets a near-deadly energy blast to the chest for her troubles.
Once she recovers, and after agreeing to go on a date with an infatuated Tony Stark, Roxanne rushes off to Vietnam to search for the missing brother of a man she met only two issues prior. As if all that wasn’t enough, it is Roxanne’s dedication to pacifistic resistance that prompts Tony to stop manufacturing weapons, a decision now considered to be at the core of Iron Man’s character.
It would appear that Iron Man has a thing for the color green. In addition to being with She-Hulk, he has also experimented a bit with Gamora, the jade-skinned daughter of Thanos and easily the butt-kickingest member of the Guardians of the Galaxy. She once described herself as “the deadliest woman in the whole galaxy,” and you’d be hard-pressed to find anyone stupid enough to argue with her on that point.
Gamora and Tony’s liaison took place during Tony’s time with the Guardians, after a bit of flirting over drinks in an intergalactic dive. Neither of them is particularly impressed with the other’s bedroom prowess, and Gamora quickly returns to what she’s best at: making sure that everyone who even thinks of doing her harm doesn’t live long enough to regret it.
Which of these women do you think is the deadliest? Let us know in the comments!
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