From all the X-Men movies, including the acclaimed “Logan,” to animated series like “X-Men ’97,” Wolverine is one of the biggest fan-favorite Marvel superheroes. With razor-sharp indestructible claws and an accelerated healing factor, James “Logan” Howlett is a killing machine with a conscience, finding his place among the mutant superheroes, the X-Men. Wolverine comes from an especially dark past, however, while his berserker rage and susceptibility to mind control makes him a lethal liability at times. This has led to Wolverine committing several especially heinous acts, some deliberately, across the character’s extensive history in comic books, television, and film.

Wolverine may be one of the greatest heroes of the Marvel Universe, but you can bet that his hands are dirty with all the questionable things he’s done. Here are the worst things Wolverine has ever done, be it mistakes made in the comics, movies, or beyond, adding to the superhero’s conflicted morality and background.

Stabbed Rogue in the chest in X-Men

Wolverine is constantly at war with his own mind, mulling with the severe mental and physical trauma he’s endured along with suffering from acute amnesia. Rogue learns the hard way just how violently troubled Wolverine is in a pivotal scene in 2000’s “X-Men.” Logan takes Rogue under his wing after encountering her as a drifter in Canada before the two are rescued by the X-Men from the Brotherhood of Mutants.

Frightened by her new surroundings, Rogue checks in on Logan while he’s sleeping in the X-Mansion, seemingly having a nightmare. Instinctively, upon waking suddenly, Wolverine extends his indestructible claws, causing him to stab Rogue through the chest. As Rogue sits in shock and pain from the accidental attack, Rogue touches Wolverine with her bare hand to allow her mutant absorption abilities to drain his healing factor and save her life. Subsequent prequels revealed this wasn’t the first time Logan hurt those he cared for in his sleep, nor would this incident be the last.

Infiltrated the X-Men to destroy them in Ultimate X-Men #1-6

Marvel Comics launched the Ultimate Universe in 2000 as a clean entry point for readers to their biggest properties without decades of convoluted continuity. Among the early titles was “Ultimate X-Men,” initially helmed by “Kick-Ass” creator Mark Millar and brothers Adam & Andy Kubert in 2001. This run reimagined many of the mutant characters in a darker, edgier light to reflect modern sensibilities, including its handling of Wolverine. This version of Logan fell in with Magneto before the X-Men and was dispatched by master of magnetism to infiltrate the X-Men and assassinate Charles Xavier.

“Ultimate X-Men” leans hard into the villainous and more controversial possibilities of Wolverine’s status quo in this new continuity, including having Logan seduce a teenage Jean Grey. Wolverine also reprograms the Danger Room to create a simulator where he brutally murders the X-Men to prepare for his true mission, to Xavier’s obvious concern. Eventually, Wolverine has a change of heart and joins the X-Men against Magneto, but definitely starts his association with them in this universe on a morally compromised start.

Broke the space-time continuum in Age of Ultron

Wolverine is no stranger to time-travel and exploring alternate universes, but he completely violated the rules of the space-time continuum in “Age of Ultron.” As opposed to the 2015 movie in the Marvel Cinematic Universe, the 2013 comic book crossover event began in a version of the Marvel Universe conquered by Ultron. With all hope lost in saving this timeline, Wolverine and the Invisible Woman decide to travel back in time to stop Ultron from being created in the first place. The storyline, created by Brian Michael Bendis and Bryan Hitch, saw Wolverine cause not one but two temporal paradoxes, each with grave consequences.

Wolverine alters history by murdering Hank Pym before he can create Ultron, only to discover that a timeline without Pym’s other contributions results in a violent dystopia. In response, Wolverine travels back in time again, preventing himself from killing Pym, but having a failsafe program installed in Ultron to defeat him before he can conquer the world. These actions put too much stress on the space-time continuum, causing tears throughout the multiverse that trigger far-reaching cataclysms in countless universes. The big takeaway here is don’t let the hero with the murder claws anywhere near Doc Brown’s DeLorean. Could this serve as the inspiration for the new Logan we get in “Wolverine & Deadpool,” where he’s responsible for something tragic in his own universe?

Went on a rampage against SHIELD in Wolverine #20-31, Vol. 3

Wolverine has an unfortunate tendency to be mind-controlled by sinister figures, even beyond his time in the Weapon X program. In the “Enemy of the State” storyline by Mark Millar and John Romita, Jr., starting in “Wolverine” #20, Vol. 3, Wolverine reverted into a programmed killing machine again. Captured by the ninja cult known as the Hand, Wolverine was brainwashed to serve them and sent to attack S.H.I.E.L.D. and the superhero community. This led to battles against heroes like Elektra (who is rumored to be appearing in “Deadpool & Wolverine”) and the Fantastic Four before the out-of-control Wolverine turned his attention to the X-Men.

In addition to scores of S.H.I.E.L.D. agents, the biggest victim of Wolverine’s Hand-orchestrated rampage was the mutant speedster Northstar. Wolverine kills the Canadian hero in “Wolverine” #25, Vol. 3 before he is captured by S.H.I.E.L.D. and has his mind restored. Though Wolverine gets his revenge on the Hand and Northstar is eventually resurrected and similarly restored to his senses, the incident reminded Logan how easily he could be manipulated.

Tried to murder Cyclops over Jean Grey in Ultimate X-Men #29

Though Wolverine presumably had a change of heart in “Ultimate X-Men” and abandoned Magneto to truly side with the X-Men, he still was prone to bouts of villainy. The most morally questionable thing Ultimate Wolverine ever did was in “Ultimate X-Men” #29 by Mark Millar and Adam Kubert. While on a mission in the Savage Land with Cyclops, things came to a head between the two men over their mutual love for Jean Grey. When Cyclops was dangling precariously on the edge of a cliff, Wolverine intentionally dropped him to his presumed death rather than hoist him up.

Wolverine reported Cyclops was killed in action in the Savage Land, leaving the X-Men reeling over the loss. Fortunately, Cyclops survived the fall but was badly injured from the impact before being rescued by Magneto’s Acolytes, who didn’t initially recognize him. Recovering, Cyclops provided pivotal support to stop Magneto’s latest attack on humanity before getting his revenge on Wolverine, beating him and kicking him off the team. Cyclops later forgave Wolverine and Logan never did anything this heinous to his fellow heroes ever again.

Wiped out the X-Men by himself in Wolverine #70, Vol. 3)

Teaming up with his old “Civil War” collaborator Steve McNiven, Mark Millar told his final Wolverine story to date with “Old Man Logan.” Running in “Wolverine” #66-72, Vol. 3, before ending in a super-sized special issue, the story is set in an alternate future for the Marvel Universe. Logan has long since retired his Wolverine persona as he lives in a dystopian world ruled by supervillains, even refusing to pop his signature adamantium claws for any reason. Through flashbacks, it is revealed what caused Logan to abandon Wolverine on the fateful night that the supervillains organized and conquered the world decades ago.

As the ambitious assault began, Wolverine believed the X-Mansion was under attack by an army of supervillains and cut them all down. In reality, the incident was an illusion created by Mysterio, with Wolverine killing all his fellow X-Men single-handedly instead. Through this story, Millar echoes his previous themes of Wolverine being a lethal liability for the entire Marvel Universe and easily susceptible to manipulation. Though mind-controlled and set in an alternate universe, the twist is still one of the most shocking moments in a Wolverine story to date.

Served Apocalypse as a Horseman of Death in X-Men #96, Vol. 2

Wolverine has fallen in with the wrong crowd plenty of times, but his most controversial was with the mutant supervillain Apocalypse (who is much better than his big screen adaptation would have you believe). Wolverine was kidnaped in “Uncanny X-Men” #371 and replaced with a Skrull imposter. In captivity, Wolverine defeated Sabretooth in a fierce duel and was selected by Apocalypse to become his new Horseman of Death in “Wolverine” #145. In this new role, Wolverine battled the X-Men on multiple occasions and went as far as attempting to kidnap Colossus as part of Apocalypse’s plans for global domination.

Initially fighting against the X-Men under a mask, Wolverine stood revealed as a Horseman of Apocalypse in “X-Men” Vol. 2 and had his mind restored as the X-Men battled Apocalypse shortly thereafter. Wolverine’s time serving Apocalypse led to his skeleton being rebonded with adamantium after it was previously stripped from him by Magneto. Compared to other instances when Wolverine was brainwashed, his association with Apocalypse had a mercifully low body count but still haunted him for some time.

Creeped on Jean Grey and Mary Jane Watson in Marvel Knights: Spider-Man

The love interest that Wolverine is most commonly linked to, in the vast majority of X-Men multimedia depictions, is Jean Grey. However, Jean is usually already romantically linked to Cyclops in these stories, and in some incarnations, like the X-Men movies, married to him. This often doesn’t deter Wolverine, who actively flirts with Jean, sometimes right in front of her spouse, not respecting the couple’s boundaries. “X-Men ’97” wisely tempers this by having Wolverine gently turn away Jean during her marital troubles, but many stories don’t take this direction.

Even more morally questionable is Wolverine’s unhealthy fixation on Mary Jane Watson in both the main Marvel comic book universe and its Ultimate Universe counterpart. In the main Marvel Universe, Wolverine hits on Mary Jane in front of Peter Parker at Avengers Tower, prompting him to throw Wolverine out a window. In the Ultimate Universe, Wolverine tries to hook up with a teenage Mary Jane after switching bodies with Peter, raising even more red flags for this dynamic. Simply put, Wolverine is an unrelenting creeper who needs to learn how to take no for an answer.

Quit the X-Men in X-Men: The Animated Series

Wolverine has often had problems with authority, which hampers his ability to play well with the rest of the team. On multiple occasions in the original run of “X-Men: The Animated Series,” Wolverine temporarily quits the team, either for selfish reasons usually stemming from his romantic frustrations with Jean Grey. In the fourth season of the original animated series, Wolverine took a particularly long hiatus from the team, when he found it harder to control himself.

On the one hand, especially seeing all the times Wolverine has grown murderously out of control, knowing to avoid becoming a liability is a noble move. However, the reasons why Wolverine leaves the team are revealed to be things that have been plaguing him since before the events of the series. One can applaud Logan for eventually confronting his unresolved trauma from the Weapon X program, but he did put this off for years. This made Wolverine a big ticking time bomb that could’ve threatened the well-being of the entire team.

Killed his own children in Wolverine #14, Uncanny X-Force #34

As prolifically passionate as Wolverine has been for decades, it should come as no surprise that he has fathered a number of children over the years. However, Logan has developed something of a reputation of being an absentee father, causing a bloody escalation years later. A cabal who swore vengeance on Wolverine for murdering their loved ones started an organization known as the Red Right Hand, tasking a group of hardened killers to attack Wolverine. After Wolverine killed them all in “Wolverine #14, Vol 4,” the assailants were revealed to be his children, handpicked by the cabal as the ultimate revenge.

However, the most contentious dynamic Wolverine has with any of his children is his long-lost son Daken, who grew up to become a murderous psychopath. Daken tormented his father after the two were reunited, even going as far as to publicly pose as Wolverine to tarnish Logan’s heroic legacy. Though Logan was determined to redeem his son, this noble aspiration failed when the two had a final showdown in “Uncanny X-Force” #34. After a grueling fight, Logan drowned Daken in a puddle, bringing this complicated father-son dynamic to a grim end.

Murdered his first love, Rose in Origin

Logan’s traumas stemming from his powers go back long before he was ever ensnared by the Weapon X program, dating back to his 19th century childhood in Canada. The 2001 comic miniseries “Origin” by Bill Jemas, Joe Quesada, Paul Jenkins, and Andy Kubert revealed Logan’s troubled upbringing. After going on the run following the reveal of his bone claws, the only person to show Logan any kindness was his childhood friend Rose. However, like so many people in Wolverine’s life, this innocent friendship and unrequited romance would be tragically cut short.

To make money quickly to support him, Rose, and Rose’s love interest Smitty, Logan began fighting in underground cage fights. During a scuffle with his vicious half-brother Dog, who spent his life tracking Logan for killing their father, Rose is pushed into the fray by the crowd around them. This coincides with Logan drawing his bone claws, with Rose fatally impaled on them in the unruly confusion. The guilt from murdering Rose drives Logan into a feral fugue state and he lives in the Canadian wilderness for a prolonged period.

Slashed Kitty Pryde during a pivotal mission in X-Men: Days of Future Past

Just as Wolverine stabbed Rogue while barely lucid in 2000’s “X-Men,” he grievously injured another teammate while in a similar state in 2014’s “X-Men: Days of Future Past.” The movie introduces the ability for Kitty Pryde to transport someone’s consciousness into the past through her phasing powers. Living in a timeline devastated by Sentinels programmed to eradicate mutants, the X-Men decide to send Wolverine back in time to change history and prevent the Sentinels’ dominance. As the X-Men defend their remote mountain base from Sentinels, Kitty maintains a vigil over Wolverine as his consciousness takes over his body in 1973.

However, right at a conveniently crucial moment, Wolverine begins to lose control of his body in the ’70s, causing his body to violently go out of control in 2023. Due to her proximity, Kitty is slashed in the torso by Wolverine’s errant claws before she can solidify his mental presence in 1973 and keep him restrained. In the alternate cut released on home video, Kitty’s injuries are so bad that the X-Men free Rogue from imprisonment to fill in for Kitty to keep Logan in the past. One hopes that, outside of post-apocalyptic scenarios, Logan sleeps under a very heavy weighted blanket to keep this from becoming a recurring incident.

Starred in X-Men Origins: Wolverine

Not all X-Men movies are created equal, but one widely regarded as being at the bottom of the barrel is 2009’s “X-Men Origins: Wolverine.” A prequel that falls in the middle of the X-Men movies timeline, the story reveals how Logan endured the machinations of Colonel William Stryker and his Weapon X program to transform into Wolverine. But the movie was widely lambasted by fans and critics alike, even its own director Gavin Hood. From its convoluted storytelling to poor digital visual effects, “X-Men Origins” was rightfully skewed for its handling of Deadpool in his live-action cinematic debut. For whatever reason, the movie decided to take away Deadpool’s signature charm — his snarky wit — and remove it by literally eliminating the character’s mouth.

Deadpool’s character assassination aside, “X-Men Origins” commits plenty of other cinematic fumbles in the name of Wolverine over its runtime. Another glaring plot hole is the movie explaining Logan’s amnesia as the result of bullets, specifically designed to pierce his skull without killing him but instead causing permanent brain damage. Of all the terrible things Wolverine has done, having his name attached to this cinematic train wreck — a strong contender for the worst of Fox’s X-Men movies — is the character’s true low point.