Let’s face it: as much as everybody loves Deadpool, the guy is kind of a rogue. Granted, he’s a lovable rogue, and the things he does to other people in the comics and movies are mostly just done for the good of comedy. And it’s hilarious!

That said, Wade Wilson generally goes around haphazardly destroying things (and sometimes even people) without any regard for others’ property or safety or emotions. If Deadpool wants something, he’ll go to any lengths to get it no matter how many people try to stand in his way!

We often forget that, despite the fact that he’s a beloved superhero today, Wilson got his start as a villain before morphing into a morally grey character and then finally into the plucky anti-hero we all love to root for.

With the title of “anti-hero” comes the association that a character exists in that grey area between good and evil. Sure, they aren’t going to go off on a crime spree for fun, but they’re also probably not going to try and save the world unless there’s a payment involved. Even then, the character isn’t afraid to get their hands dirty and do some questionable things that most superheroes wouldn’t do. These kind of shady things are all over Wade Wilson’s resume!

Try as he might to remain on the straight and narrow, Deadpool can’t help but revert back to his anti-hero ways whenever the situation becomes dire.

Here are the 15 Worst Things Deadpool Has Done.

His mistreatment of Hydra Bob

Though he isn’t as frequent in the pages of Deadpool as characters like Cable, Domino, and Blind Al, Hydra Bob is a fan-favorite of those who love the Merc with a Mouth. Bob doesn’t really believe in the propaganda and mission of his employer like some of its other members. He just took the job because it had good benefits for his family!

Cable and Deadpool came across Bob while they were trying to escape from the evil organization while on a mission. Though their first encounter was a little rocky (to say the least), Wade calls up Bob whenever he needs a sidekick for one of his adventures. The character even got a surprise cameo in the 2016 Deadpool flick as just “Bob” (since Disney owns the movie rights to Hydra, not Fox).

The thing is, this relationship is horribly one-sided! Though Bob has grown to like Deadpool over time, he suffers constant abuse from his partner. The first time the two met, a miniature-sized Wilson used a keycard to torment the agent of Hydra for information and then forced him to fly an escape jet to safety despite the fact that he didn’t have any piloting skills.

Deadpool likes to smack Bob around for kicks and giggles and has shot him in the hand, forced him to ride on the outside of a moving aircraft (causing him to fall), and has submitted him to mental torment after mental torment.

He injured an innocent man to escape

Deadpool is known as one of the funniest superheroes around, never taking anything seriously and cracking jokes as he gleefully causes chaos. Daredevil, on the other hand, is the polar opposite of Wade Wilson; he’s precise, subtle, and treats his crimefighting job like it is a holy mission. This is why writers thought it would be hilarious to put the two at odds in the pages of Deadpool #11.

While pursuing a target with the power to shape-shift, Wilson’s enemy turns into popular superheroes like Black Widow and Luke Cage. This leads to the police thinking Wade has finally snapped, forcing our hero to go on the run himself. While he is running down his target, Matt Murdock appears to bring the Merc down.

The two heroes start to tangle, and Deadpool realizes that, despite his excellent training and mutant powers, he is no real match for Daredevil.

Instead of conceding the fight to Daredevil, Deadpool gets a sinister idea.

A bunch of civilians were gathering around to watch the spectacle, and one of them was the Merc’s ticket to freedom; Deadpool uses his gun to shoot a man in the leg. Though the wound isn’t instantly fatal, he hit a major artery. This forces Daredevil to make a choice: take the man to the hospital and let Deadpool get away, or keep fighting Deadpool and let the man bleed out. Being a hero, Murdock chooses the former and Wilson is able to slip away.

X-Men Origins: Wolverine

Sorry, Deadpool fans. We can’t get through this list without talking about the disastrous X-Men Origins: Wolverine. This was supposed to be the best X-Men film ever made.

It was a solo film about Wolverine that was going to explore his backstory, his relationship with Victor Creed, and his time in the Weapon X program while also featuring a huge cast of characters from the larger Marvel lore. The casting seemed spot on, as well; Liev Schrieber as Sabretooth, Taylor Kitsch as Gambit, and Ryan Reynolds as Deadpool were all perfect representations of the characters. In the first act of the film, despite his handsome face, Reynolds seemed perfect as the Merc with the Mouth!

Then we got the film’s climax. Wolverine and his allies show up to save a large group of mutants from Colonel Stryker’s sadistic experiments, only to come face-to-face with a brainwashed Wade Wilson - who had his mouth sewn shut, blades that came out of his arm, and could teleport and shoot lasers out of his eyes. Who green lit this?

Ryan Reynolds (a huge fan of Deadpool) was so upset that he allegedly almost lost the role for speaking up about how terrible it was. In Deadpool, the controversy is acknowledged when the camera zooms in on an action figure from the movie while Wade talks about the darkest period of his life.

He keeps testing Mr. Immortal’s powers

Mr. Immortal is one of the weirdest characters in the Marvel comics. One of the founders (and the leader) of the Great Lakes Avengers, the character is endowed with a unique ability: the power to always come back from the other side, no matter how gruesome of an end he meets. This leads to Mr. Immortal constantly sacrificing himself for the greater good.

Though this power is normally played for laughs like Deadpool’s healing ability, it has also led to some darker moments in which the character wrestles with the stress of constantly passing and returning as well as questions his sanity.

Of course, when Deadpool crosses paths with the Great Lakes Avenger, things go from zero to one hundred very quickly! Both being the subject of humorous titles, the two characters have interacted a surprising number of times. Once, Deadpool tried to apprehend the GLA when he thought they hadn’t registered for the Superhero Registration Act. Another time he took up residence in their headquarters and wouldn’t leave.

Every time they interact, Deadpool tries to push Mr. Immortal’s powers to the limits; the Merc with a Mouth has ended his fellow hero in an abundance of creative ways without any remorse.

Deadpool sucker-punched Kitty Pryde

Deadpool and Wolverine go together like peanut butter and olive oil. Despite both being part of the Weapon X program, both coming from Canada, and serving on several teams together, Logan absolutely hates Wade Wilson. Wolverine is a notoriously grumpy character; he’s the best he is at what he does, after all, and what he does isn’t very nice!

This hatred is one-sided, however, as Deadpool loves working with Wolverine. Or more particularly, he loves antagonizing the grumpy X-Man. Since they both have healing powers and love to use sharp weapons, any battle between the two characters is bound to be gruesome.

During a short story arc in the first volume of the Deadpool comics, Wade Wilson goes to the ridiculously-named Dr. Bong for therapy. The former Howard the Duck villain recommends to Wade Wilson that he should get out his aggression through what he calls “fighting therapy.” Wade realizes that the only person he can fight with full force without the risk of ending them is Logan, so he goes off to Japan to find the hero, who is with fellow X-Man Kitty Pryde.

Despite his best efforts to antagonize Wolverine, he doesn’t get the guy to bite. In a last-ditch effort, Deadpool savagely uppercuts Pryde while exclaiming “Shoryuken!” This finally works, and Logan and Wilson fight across the rooftops of Japan.

His offensive disguise

Even if Iron Fist and The Defenders received less-than-stellar reviews, Iron Fist and Power Man are still the most iconic duo of the Marvel universe!

In the ’70s, sales of both of the characters’ solo titles were in the garbage; to rectify the issue, Marvel put the two together in the pages of Heroes for Hire, and the rest is history! The new series revitalized Iron Fist and Luke Cage in the eyes of readers thanks to some clever writing and the great chemistry between the two heroes that were so drastically different.

During the run of volume 3 of the Deadpool comics, the writers thought it would be fun to throw in a “lost” issue every now and again. This was an issue that came from a different period of Marvel’s history and featured the Merc with a Mouth interacting with the version of the characters that existed at the time. Issue #13 saw Wilson travel back to the ’70s, where he teamed up with Iron Fist and Power Man.

Deadpool tries to go undercover as a street-smart, jive-talking man decked out in a large fur coat and a ginormous hat.

Where do we even start with this one? As funny as it might be to witness, the way ‘Pool acts while he is undercover makes even the most desensitized person cringe!

His love for Star Wars went too far

There is a large crossover of people who love Star Wars and people who love Deadpool. Why wouldn’t there be? Both franchises are full of fun and clever writing, and are much more lighthearted than other popular geek franchises. It’s only natural that the writers of Deadpool would also share a love for the sci-fi saga.

The Merc with a Mouth is constantly making references to the galaxy far, far away in all forms of media.

The Star Wars Prequels are a touchy topic among the fans. Some think they are the worst things ever made, while others like to point out that, while they may be inferior to the Original Trilogy, they still have a ton of heart and some awesome scenes and characters.

With Deadpool, the issue is pretty black and white: he’s a prequel hater. During one of his encounters with the evil organization AIM, Wilson holds two henchmen captive and forces them to fly him towards his objective. As they approach their destination, Deadpool makes a reference to Han Solo’s “fly casual” comment in Return of the Jedi. Almost instantly one of the henchmen interrupts, claiming that he prefers the prequels to the original trilogy and that he thinks Hayden Christensen is an amazing actor. Without hesitation, Wade shoots him and then turns the gun on his friend, telling him to proclaim Jar Jar Binks as an abomination!

He eliminated Phil Coulson

Who doesn’t love Phil Coulson? The Agent of S.H.I.E.L.D. was an original character created for the MCU and portrayed by Clark Gregg. The agent became a fan-favorite during Phase One, which made it all the more painful when he met his end at the hands of Loki in The Avengers. Of course, he was brought back thanks to some movie magic (aka Tahiti) for the Agents of S.H.I.E.L.D. TV series, but Gregg hasn’t appeared in an MCU film since. His character became so popular that Marvel eventually translated him into the comic books!

Unfortunately, comics Agent Coulson had a similar fate as his big-screen counterpart in store. During the Secret Empire story line, it was revealed that Captain America was a secret agent of Hydra his entire life and planned on decimating the Earth with an alien invasion. To make sure that his scheme went off without a hitch, Rogers enlisted a group of morally-grey heroes and villains to form a new Avengers team.

Deadpool jumped at this opportunity to work with his hero. His first task? To eliminate Phil Coulson, who had discovered Steve’s dirty little secret. Despite Agent Coulson’s pleas, he is taken out by the Merc with a Mouth.

Deadpool stole the Hulk’s blood

The Hulk is arguably the strongest superhero in all of fiction. Whenever people debate who would win a fight, they usually end up comparing the characters in question to the Hulk or Superman or Goku. The craziest thing about the Incredible Hulk? The angrier he gets, the stronger he gets. This means that no matter what you throw at the behemoth, he’s going to get right back up and be stronger than ever! Hulk is only ever truly defeated when he goes up against magic users who can trick him or is turned back into Bruce Banner - neither of which are common occurrences!.

This is exactly the case in Deadpool #4. After being exposed to gamma radiation, Wade starts to notice that his healing factor isn’t working like it used to. After talking with Dr. Killebrew, the Merc realizes that he needs a sample of the Hulk’s blood to reverse the effects.

This leads to an epic brawl in which ‘Pool antagonizes Bruce Banner into becoming the Jolly Green Giant. However, Deadpool can’t seem to get the creature to bleed. The solution?

Deadpool launches the Hulk into the air and then places a jagged street sign post under his landing spot.

This may not be as terrible as some of the other entries on this list, but to torment poor Dr. Banner and then physically injure him is pretty despicable.

He lobotomized his friend

Cable and Deadpool are the odd couple of the X-Men universe. They are two sides of the same coin; Cable is stoic and no-nonsense, while Wade is snarky and all-nonsense!

Despite this, they both are equally skilled in hand-to-hand combat and weapon handling. They famously teamed up for the hit comic series Cable & Deadpool in the early 2000s, and Nathan Summers makes his big screen debut in Deadpool 2. Much like Luke Cage and Iron Fist, the pairing of these two characters seems to work thanks to their bizarre chemistry and awesome friendship.

The relationship between Cable and Deadpool is not all sunshine and rainbows.

Their drastically different personalities and methods put them at odds with each other constantly, as was the case in the first major arc of their self-titled comic book. In this story, Cable gains a large number of followers and brings them to a floating island to start a new nation. He then threatens to destroy the worlds’ nuclear weapons; this forces many nations to plan an attack on the island. Deadpool stops this insane scheme when he uses his broken teleporter to lobotomize his friend, saving his life yet causing him great pain in the process.

He eliminated the entire Marvel universe

Yeah, you knew this was going to be on the list at some point! This is probably the biggest “What If?” story in Wade Wilson’s history.

It starts with Deadpool having medical issues and being rushed to a hospital. While there, the villain Psycho-Man tries to brainwash him, but fails and turns Wilson even more insane than he already was. The voices in Deadpool’s head suddenly turn from happy and zany to dark and violent; he offs Psycho-Man and decides to rebel against his comic book creators by eliminating the entire Marvel Universe. This leads to a series of gruesome encounters with fellow superheroes in which they all end up on the wrong side of the Merc’s weapons.

In this comic, Wade is able to bring down the Fantastic Four, Spider-Man, Wolverine, Thor, and the entire cast of the Avengers!

After the entire Marvel Universe has been wiped out, Deadpool sets his sights on other literary characters. He begins hopping across different works of fiction such as Moby Dick and The Jungle Book, eliminating every major character within their pages. In the end, he goes after the comic book writers themselves!

Eventually this alt-universe version of the character comes face to face with the Wade Wilson of our world, who is able to defeat “Dreadpool” thanks to the help of the Deadpool Corps before he can tarnish his reputation any further.

Wade let Vanessa think he’d lost his life

2016’s Deadpool was a surprise hit for just about everybody. Many fans were excited for an R-Rated version of the character, but were worried that the rating would shrink the potential audience and hurt box office returns. Instead, the movie shattered records, becoming the biggest R-rated movie in history as well as the most successful February opening ever.

The film’s entire plot revolved around Wade Wilson’s relationship with Vanessa (Copycat in the comics), a woman who could match the Merc’s ridiculous sense of humor and wacky personality perfectly.

However, when Wade gets sick from his cancer, he makes the difficult choice to go off and join a mysterious experimental treatment despite her protests. Of course, he doesn’t tell Vanessa this.

He just leaves her in the middle of the night so that she won’t have to go through the pain of losing him.

Once he is cured of his cancer and becomes the Deadpool we all know and love, Wilson still doesn’t reveal to his girlfriend that he is alive! Afraid that she’ll think he’s a monster, Wade simply keeps letting her think that he’s gone. It takes Vanessa being captured by Ajax to finally bring this revelation to the light.

Deadpool made fun of Tony Stark’s addiction

Though the MCU might be one of the biggest franchises in movie history and Iron Man sits at its front and center, the series has shied away from Tony Stark’s most famous storyline.

During the Demon in a Bottle arc, Stark’s love of alcohol finally gets the better of him. The hero realizes that he’s an addict and that it’s destroying his body, so he takes a temporary leave from being Iron Man. In his place, James Rhodes steps up and becomes Marvel’s Golden Avenger.

Tony’s battle with addiction is very briefly hinted at in Iron Man 2, where it shows the character checking his BAC before an event and then later getting reckless with his tech while intoxicated.

In another one of Deadpool’s “lost” issues, the Deadpool of the ’70s is met by a demon who wants Tony Stark to get hooked back on the sauce.

Wilson initially complies, grabbing a bunch of bottles and making his way to a hotel where Iron Man is staying. Though he doesn’t actually go through with the sinister plot, he knocks out Tony when a nuclear crisis occurs and dons the suit of armor himself. As he flies through the air, ‘Pool makes sure that everyone sees that Iron Man is visibly intoxicated, poking fun at Stark’s demons and hurting Iron Man’s reputation in the eyes of the public.

He used his own daughter as bait

Believe it or not, Deadpool is a daddy! In his younger years, the anti-hero was in a relationship with a woman named Carmelita Camacho. Unknown to Wade, Carmelita was pregnant when he dumped her; she raised the child alone and kept her hidden from Wilson until she wanted him to pay child support.

Though the girl is aware of her father’s existence, Deadpool feels it would be better for everyone if he kept his distance. Madcap is a D-list Captain America villain who has become one of the Merc’s go-to adversaries over the years; he has the unusual ability to use mind control on people who are highly emotional as well as a powerful healing factor like Deadpool himself.

In one particular comic book story, Madcap was able to impersonate the Merc with a Mouth; he went around the city threatening Deadpool’s allies and causing mass chaos in order to turn the public against Wade Wilson. Once the real Deadpool discovered why he was getting such a bad rap, he decided to confront the villain.

In order to bring Madcap out, he used his daughter Eleanor as bait.

This act put his only flesh and blood directly in the path of danger, and the girl was only saved thanks to the aid of fellow X-Man Quicksilver.

His entire relationship with Blind Al

Blind Al has to be one of the strangest characters in all of comics, and that’s saying something! As her name implies, Blind Al is a blind woman who shares an apartment with Deadpool. She often plays the role of the “sarcastic voice of reason” in the series, hurling insults at Wilson whenever he wants to do something stupid and matching his wit word-for-word.

In the Deadpool movie, the character was played by actress Leslie Uggams, who received much praise for her short yet memorable role.

In the comics, the relationship between Blind Al and Wade Wilson is bizarre, to say the least. Some versions show the two as just roommates who barely tolerate each other, yet rely on each other to pay their half of the rent.

In most comics, Blind Al is Deadpool’s prisoner; he refuses to let her leave the house and will end anyone who tries to help her escape.

Think that’s bad? Whenever Al would annoy Wilson, he’d find a new way to torment her. He once locked her in a small box full of pointy objects and told her to feel her way out. The one time that she did escape, Al went to her friend’s house, where she found Wilson waiting for her with her injured friend. This is our favorite hero?

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What are some other shady things that Deadpool’s done? Let us know in the comments!

  • Deadpool 2 Release Date: 2018-05-18