Top 10 Superheroes Who Slept with Villains (Marvel and DC)

Even though the two sides oppose one another, there are some instances where those who oppose one another actually develop feelings for each other. Yep. There are some superheroes out there who have taken the plunge and become romantically involved with their villainous counterparts. And it’s not hard to see why. Being a villain adds a certain level of mystery to who they are.

I mean, it adds another layer of intrigue to their already sexy exteriors. As the saying goes, opposites attract and heroes and villains are as opposite as they come. Comic books have done a great job of pairing up heroes and villains over the years. Some relationships are expected to happen while others take us, readers, by surprise. If you’re wondering who they are, stay with me for a minute and I’ll tell you. Here are the top 10 superheroes who got romantically involved with villains.

10. Wolverine (Mystique)

First meeting in 1921, the history between Wolverine and Mystique is as long as it is complicated. During this time, the two belonged to the same gang. While members, the two friends eventually became lovers. Unfortunately for Wolverine, their “relationship” ended when Mystique purposely pushed Wolverine from a train.

After the train incident, things became, shall we say, heated? Shortly after the train incident, Mystique and Wolverine’s arch-nemesis, Sabretooth hooked up, had a child who became a mutant hater, and then split. If there was ever a chance that Wolverine and Mystique could get back together, that chance ended with the birth of Graydon Creed.

9. Iron Man (Madame Masque)

It’s interesting that of all the women Tony Stark has dated, very few have the allure that Madame Masque has. Madame Masque is actually Whitney Frost and Whitney Frost is actually the daughter of Count Nefaria. As Count, Nefaria commands that Whitney must become the leader of the Marvel Comics version of the mafia called the Maggia.

Her leadership, however, wasn’t meant to be. Shortly after the Count made his demand, Whitney was involved in a terrible plane crash. As a result of the crash, she was left horribly disfigured and forced to wear a mask. Later on, she met and befriended Tony Stark. Enamored with his selfless acts of kindness, the two begin a relationship with one another. Like most things in comics, their conflicting interests caused them to break up and never date again.

8. Green Lantern (Star Sapphire)

Although in modern-day Star Sapphire is seen more as a hero, this wasn’t always the case. Star Sapphire, Carol Ferris, is the Vice President of Ferris Aircraft. As Vice President, she was directly involved with the hiring of Hal Jordan to be one of their pilots. Once employed, it didn’t take long for the two to develop feelings for one another and begin a relationship. 

Sadly, after Hal was given a Green Power Ring and Carol was chosen to be the Queen of the Zamarons, things changed. As Queen of the Zamarons, it was forbidden for Carol to have feelings for a Green Lantern. Due to this, she was, on more than one occasion, forced to fight Hal in combat. From this moment forward, the two became enemies and Carol became a villain.

7. She-Hulk (Juggernaut)

Ok. If you’re thinking that this one is a little too unbelievable to be believed, hear me out. For a time, Juggernaut had reformed and became an active member of the X-Men. During this time, he and Jennifer Walters, the She-Hulk, actually hooked up. And if you think about it, this makes perfect sense.

There are very few people in the Marvel Universe who can, ahem, handle the Juggernaut’s power. She-Hulk, with all her strength and power, is one of those people. So, that’s exactly what they did. In one of the most bizarre panels in Marvel history, the two destroy a room in an exchange that saw him dip his corn dog in her batter.

6. Cyclops (Emma Frost)

The sight of Cyclops and Emma Frost together infuriated many longtime X-Men fans. After all, it was Emma that played an integral role in Jean Grey becoming the Dark Phoenix. I, however, am not one of those people. I actually enjoy the sight of Scott and Emma together.

For any who doesn’t know, their relationship actually started out as an affair. Now I’m not condoning the two having an affair. Not for a second. What I am condoning is Marvel comics giving Cyclops some much-needed depth to his always bland character. Emma Frost is exactly what he needed. She’s good only to a point, diabolical to a further point, and is usually playing the “what’s in it for me” game…each of which the Cyclops character could use a little more of. 

5. Invisible Woman (Dr. Doom)

There are very few characters as complex and interesting as Dr. Doom. He’s intentions are both evil and good. He wants his people to live in peace and dine in prosperity but does so at the expense of the world around him. His interests have caused him to feud with the Fantastic Four more times than I can count. Of the members of the Fantastic Four, none have caused him more pain than Reed Richards. Not only is Richards arguably more intelligent than Doom, but he also has the one thing Doom could never have Sue Storm. 

Or so we thought. During the Secret Wars event, Doom was able to take control of the Beyonders power and created a reality in which he and Sue were married. Although only temporary, this change to reality landed Dr. Doom on this list of superheroes who slept with villains.

4. Spider-Man (Black Cat)

There are few characters at Marvel who can boast (?) the history of girlfriends that Peter Parker has had. Gwen Stacy. Mary Jane Watson. Betty Brandt. And, of course, Felicia Hardy. For the purpose of this list, it’s Felicia I’m most interested in.

As you probably know, Felicia Hardy is the Black Cat and the Black Cat is one of the most notorious thieves in all of Marvel. Her name is a clever play on the word cat burglar, she dresses in all black so as to not be seen, and she’s the daughter of the high-level burglar, Walter Hardy. If it seems to make no sense that Peter would be interested in her, remember that not only is she beautiful, but she’s also mysterious…a very common form of attraction.

3. Batman (Talia al Ghul)

Well, it’s tough to make this list and not include one of Batman’s many lovers. This time, rather than hooking up with Selina Kyle, ol’ Bruce Wayne took an interest in the daughter of arguably his greatest enemy, Talia al Ghul. 

The remarkable thing about their fling is that their encounter ended up with Talia becoming pregnant and then convincing Bruce that she miscarried the baby. Of course, she didn’t, and eventually, she gave birth to their son Damian Wayne. Talia is probably the one girl Bruce should’ve kept his hands off of but because he’s Bruce Wayne, he couldn’t and must now live with his choices.

2. Daredevil (Elektra)

The history of Daredevil and Elektra is well-known. The two attended college together and quickly fell in love. Although they didn’t know it at the time, each was a costumed vigilante. Matt Murdock was the heroic Daredevil, while Elektra was an assassin for hire. 

They eventually learned who each other were and their conflicting interests caused them to separate. Even though they still have feelings for one another, now separated, they have no choice but to stand up for what they believe in…even if it means battling one another.

1. Batman (Catwoman)

Here we go again. The world shook the day that Bruce Wayne proposed to Selina Kyle and she accepted. It wasn’t as if nobody saw it coming. Instead, it was more a collective sigh of relief followed by a “finally”. The pair have been an on-and-off-again couple for the near entirety of their existence. They conceived a child together (in another universe) and bend their own personal code of ethics for one another. Selina is the remedy to Bruce Wayne’s life and that’s exactly why, just before they got married, she called it off. 

The canceled wedding resulted in the entire DC community of fans to breakdown into tears. We had all thought that he had finally found the “one” and was ready to move into the next stage of his life. Alas, he didn’t and Gotham is better for it.

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