Marvel Comics' superheroes are best known for their humanity and relatable flaws. Even the Marvel Universe's most morally upright heroes aren't exempt from making grave mistakes or hurting their loved ones on accident. However, some heroes' sins were so heinous and questionable that they ruined their own reputations forever.

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Despite the comic creators' hopes of making a compelling story, these heroes barely recovered from the fallout that their personal failings caused. Some heroes found new life as complex anti-heroes who are now on the long road to redemption. Others never recovered, and are still hated by fans and even their creators for what they did.

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10 The Gold Goblin (Norman Osborn)

Norman Osborn saves the day in Gold Goblin

After Sin-Eater erased his sins, Norman Osborn turned a new leaf. Now, Norman spends his peaceful life raising his grandson and helping others as the new hero, Gold Goblin. Predictably, Norman redeeming himself was easier said than done. Besides everyone doubting his goodwill, Norman can't forgive himself for the atrocities he committed.

Norman knows that his heroics won't earn him his victims' forgiveness or salvation, but he's still doing his best to atone for who he used to be. It's still too early to tell if Norman tenure as the Gold Goblin will be permanent or if he will regress to the Green Goblin, but his heroic legacy was arguably already tarnished by his evil past.

9 Venom (Eddie Brock)

Venom zips through New York City in King in Black

Before he became a father and a fan-favorite anti-hero, Venom was an uncontrollable monster whose life's mission was to torment Spider-Man at every given opportunity. Eddie Brock blamed Spider-Man for his misfortunes. With the help of the symbiote, Eddie killed and injured many innocent people just to get to his nemesis.

But after a crisis of conscience and inadvertently giving birth to the more evil Carnage, Eddie mellowed out. Venom became a violent but truly just anti-hero. Despite their best efforts and recent heroics, Venom can't escape their bloodthirsty past. Eddie doesn't mind, since he just wants to do some good before his inevitable death.

8 The Punisher

Frank Castle leads The Hand in The Punisher

The best that could be said about Frank Castle was that he was created during the 1970s. During this point in time, murderous vigilantes were the rage. But if the Punisher was portrayed as an anti-hero in the 70s, his supposed heroism came under intense scrutiny or was outright stripped from him in succeeding decades.

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Whatever good the Punisher did for the Marvel Universe or individual heroes was tarnished by the fact that he was a remorseless mass murderer. It could be argued that Frank was more evil than those he killed. That being said, Frank doesn't care about making a heroic legacy because he considers himself damned to begin with.

7 Prof. Charles Xavier

Professor Xavier welcomes his newborn Mutants in House of X

To most people, Prof. X was the X-Men's altruistic leader and kindly principal of Xavier's School for Gifted Youngsters. The truth, however, was that Prof. X saw everyone as means to his end. With his psychic powers and cunning mind, Prof. X lied to and coldly used his allies, enemies, and even students to advance his agendas.

Over time, Prof. X devolved from an idealistic and kindhearted mentor to a cynical and utilitarian mastermind. Prof. X crossed the point of no return during the mutants' Krakoan era. Now, it's clear that he's willing to sacrifice everything and everyone for his utopia. Whatever goodwill Prof. X still has is thanks to his incarnations outside the comics.

6 Mister Fantastic

The Maker taunts Eddie Brock in Venom

Originally, Reed Richards was the Fantastic Four's genius leader and kindly patriarch. But in the 2000s—especially during his Ultimate run, his time with The Illuminati, and his alliance with Iron Man in the Civil War—Richards devolved from an eccentric scientist to an amoral one. This sullied his reputation inside and outside the Marvel Universe.

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Because of this unethical and pretentious mindset, Mister Fantastic seemed more like a villain than a hero. This was fully realized in the Ultimate universe, when he became the multiverse-destroying villain The Maker. Marvel made great strides to repair Richards' image and personality, but there's still a long way for him to go.

5 Iron Man

Iron Man represents America in Civil War: The Initiative

Fans gravitated towards Iron Man because he was an imperfect and troubled yet well-meaning anti-hero, but he fell out of favor after Civil War (by Mark Millar and Steve McNiven). Tony Stark Jr. siding with the government and enforcing the Superhuman Registration Act made sense, but his brutality and sanctimonious attitude angered readers.

Whatever nuance Iron Man had disappeared during Civil War. After being known as a morally complex and painfully human superhero for decades, Iron Man was forever branded an egotistic government stooge and a fascist. Marvel's creators agreed. Even today, Iron Man is still being called out and humiliated for his actions in Civil War.

4 Karen Page & Daredevil

Karen Page recognizes Matt Murdock in Daredevil

Something many Daredevil fans may not know or chose to forget about his love interest, Karen Page, was that she had a history of drug addiction. During Born Again (by Frank Miller and David Mazzucchelli), Karen sold out Daredevil's identity for some heroin. Karen made amends by fighting drugs as a lawyer and dying to save Matt Murdock.

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This was such a dark and arguably misogynistic turn for Karen that most Marvel creators didn't even want to address or attempt to undo it in Daredevil's later runs. Unfortunately, Karen's rock bottom was the only thing readers remembered for the longest time. Unsurprisingly, this subplot was scrapped in Daredevil's Netflix series.

3 Cyclops

Cyclops cries to himself in X-Factor

Cyclops already doesn't have the best reputation among X-Men fans because of his stuck-up personality, but things got worse when he was rewritten into an unfaithful romantic partner. Scott Summers' most infamous act of infidelity was when he abruptly left his wife and child the moment he heard that Jean Grey somehow resurrected.

From then on, Cyclops developed a reputation among fans for being emotionally stunted. This infamous moment was later trumped by Emma Frost tricking Scott into having an affair by assuming Jean's appearance and personality. These plus his already unlikable past turned Cyclops into one of the X-Men's most unpopular members.

2 Spider-Man & Mary Jane Watson

Mary Jane Watson and Peter Parker break up in The Amazing Spider-Man

Peter Parker and Mary Jane Watson's romance is one of the most iconic and beloved relationships in comic book history, but Peter can never seem to keep it together. Whenever things were going great, Peter and Mary Jane's relationship would implode. This was usually Peter and even some Marvel creators' faults.

Fans grew frustrated or gave up after of One More Day(by J. Michael Straczynski and Joe Quesada) and recent developments regressed Peter and Mary Jane's relationship back to zero. More critical readers saw this as Peter's inability to grow up, and his creators' refusal to let him be anything more than an outlet for their youthful nostalgia.

1 Ant-Man (Hank Pym)

Hank Pym chastises Iron Man in Secret Empire

Hank Pym, the original Ant-Man, is a founding Avenger and one of the smartest people in the Marvel Universe. However, all of his accomplishments were overshadowed by the fact that he struck his wife, Janet, during an argument. Despite the writers' attempts to recontextualize what happened, Hank was forever remembered as a wife-beater.

Domestic abuse became a core part of Hank's characterization, and the other heroes' reaction to this defined their interactions with him. This dark legacy was the reason why Hank was practically reinvented for the Marvel Cinematic Universe. Instead of a guilt-ridden wreck, the MCU Hank was a loving husband and father to Janet and Hope, respectively.

NEXT: 10 Reasons Why Wasp Is The Best Avenger