Back in 1991 in issue #98 of The New Mutants, Deadpool, the infamous Merc With the Mouth, was introduced. Almost immediately Wade Wilson changed the landscape of comic books. Whether that change was for the better or worse is up for debate another time. What matters is that he’s been a profoundly influential character. After disappearing into obscurity for a couple years, Deadpool’s come back with a vengeance over the last decade, taking the world by storm with comics, movies, memorabilia…everything you can imagine.
While Deadpool was originally more a satirical character, he’s turned into a lovable loon who’s able to get away with things like murder if only because he’s funny. Don’t let the humor fool you, Deadpool, at his core, is a dark, twisted figure who’s committed some truly horrific acts. While he tries to do good, there’s a reason many people consider him an anti-hero. Unlike many heroes, Deadpool has no problem bending his morals or avoiding them altogether like the plague. Even though Deadpool is a mercenary who will kill whoever needs killing for the right price, he’s also demonstrated moments of legitimate heroism. Today we're taking a look at the 10 sickest and most sadistic things he's ever done and 10 of his most heroic!
20 SADISTIC: KILLED PHIL COULSON
Wade Wilson idolizes Captain America. But really, who doesn’t? No matter what, Wade would follow the good Captain to hell if Steve Rogers asked. In Secret Empire, an evil Captain America effectively asks that of Deadpool. Despite Captain America committing horrible acts, Deadpool is blinded by his devotion and he won’t lose faith in his idol; his loyalty is unwavering. The dark Captain America takes advantage of Wade’s dedication and sends him to kill Phil Coulson, Agent of S.H.I.E.L.D.
What makes the situation even worse is that the reader(s) knows Phil’s time is up and every act the man takes is just prolonging the inevitable. In spite of all the good Coulson has done over the years, Deadpool doesn’t care. One bullet through the heart later, one of S.H.I.E.L.D.’s finest is dead.
19 HEROIC: FED ANGEL BITS OF HIMSELF
One of Deadpool’s most heroic acts is weirdly one of the more gruesome things he’s ever done. It’s not everyday you equate heroism with feeding another person bits of your flesh.
However, relatively early on in the Uncanny X-Force series, the black ops mutant hit squad X-Force suffers a serious beating from Apocalypse’s Four Horsemen. Among the fallen heroes is the X-Man Angel who’s slowly withering away. Deadpool saves Angel’s life by feeding him his flesh. Due to Deadpool’s advanced healing factor, he can regenerate skin tissue super fast. When he saw Angel on the verge of death, Deadpool decided the best way to save the hero was to hack off parts of his own arm and feed it to him. The plan worked and Angel was saved. Through it all, Angel asks what he was eating and Deadpool refused to tell him that Angel had effectively become a cannibal.
18 SADISTIC: KILLED CABLE
Deadpool and Cable have been friends, enemies, and back again ever since they first met in New Mutants #98. In first couple issues of The Despicable Deadpool series, Deadpool is actively trying to murder Cable. In the previous series, some of Wade’s family member’s lives were in jeopardy. To save them, he made a deal with Stryfe, an evil future clone of Cable. If Deadpool kills certain people for Stryfe, he’ll keep his end of the bargain. One person on the list is Cable.
For his part, Cable doesn’t care what Wade’s motivations are, and tries to kill the mercenary right back. Eventually, the two come to an understanding. Just because Deadpool has to kill Cable, doesn’t mean it has to be Cable from the present. The two venture off to meet Old Man Cable, Nate Summers as he’s about to die, and Deadpool puts a bullet in his head.
17 HEROIC: BEFRIENDED KID APOCALYPSE
Apocalypse is thousands of years old, one of the X-Men’s most powerful foes, and generally considered the first mutant. Believing only the strongest should live, the villain spends most of his time trying to bring carnage into the world. When X-Force, led by Wolverine, caught wind that an Apocalypse cone had been made, they hunted him down. The mutant Fantomex then mercilessly killed him.
Afterwards, because he felt bad, Fantomex took some of the blood, and cloned Apocalypse; the result was Evan Sabahnur, or Kid Apocalypse. Accepted into the School For Gifted Mutants, one night Deadpool sneaks into Evan’s window and gives the young mutant a good talking-to. Wade wants Evan to remember the goodness in his heart and that no matter what, Deadpool will always consider him family and have the boy’s back.
16 SADISTIC: USED HIS DAUGHTER AS BAIT
Many people, including superheroes, make for exceptional parents. Deadpool is not one of these people. While most parents would shudder at the idea of putting their kids in harm’s way, Deadpool figures why the heck not?
Deadpool has the tendency for becoming obsessive over certain matters. When the villain Madcap was running around, Deadpool went to any and all lengths to fight and capture him; that included using his own daughter as bait. Granted, Madcap is a bad guy who’s potentially far more dangerous than Deadpool could ever hope to be, but Wade had only recently discovered his daughter, and was already quick on making use of her. Despite Deadpool’s intent in trying to stop a bad guy, the way he did it was pretty despicable. Thankfully, the hero Quicksilver was nearby and saved her.
15 HEROIC: SAVED SPIDER-MAN'S SOUL
Itsy-Bitsy was the genetic offspring of both Spider-Man and Deadpool. After appearing in Spider-Man/Deadpool, Itsy-Bitsy made it her personal mission to murder in the name of her two daddies. Try as they might, the combined efforts of Spidey and Deadpool proved insufficient to take her down. They found themselves outclassed multiple times, with Itsy-Bitsy reveling in pushing Spider-Man emotionally, making him desperate.
After a while, Spider-Man decides to murder her. Deadpool, realizing his friend’s essence and soul is in trouble, does everything possible to save Spider-Man from committing a horrible deed. Part of the problem revolved around Mephisto, the literal devil, tampering with Peter’s soul and making him especially moody and nasty. Yet, at the cost of his own sense of newfound heroism and personal identity, Deadpool is able to save Spider-Man’s humanity.
14 SADISTIC: SHOT SPIDER-MAN IN THE HEAD
In Deadpool Kills the Marvel Universe, the super-powered mercenary does just that. In exceedingly gruesome ways, Deadpool kills everyone, including teams like the X-Men, and even the child heroes Power Pack. It was a savage side of Deadpool many people hadn’t seen before.
After killing some villains, the first hero Deadpool murders is Spider-Man. Peter Parker confronts Deadpool and attempts to reason with him. Initially, it looks like Spider-Man has the upper hand, but Deadpool, the sneaky bugger that he is, takes out a gun and shoots Spider-Man in the face. There were many disturbing moments in the series, but Spidey’s death was arguably the most shocking. Rarely had such a brutal act ever been taken towards towards Spider-Man. It was even more alarming considering the web-slinger is Marvel’s prized and most iconic hero.
13 HEROIC: TALKED SOMEONE DOWN FROM A LEDGE
If there’s one person who understands genuine suffering, it’s Deadpool. Though an unlikely candidate for suicide prevention, there’s arguably no other hero who’s better qualified. Wade Wilson has been the subject of horrible experiments, everyone hates him, and his life is generally a massive garbage fire. Wade, despite his manic behavior, understands the value of life and moving forward in the face of hardship.
In Deadpool #20, Deadpool stops Danielle, a young woman, from jumping off a building. He knows he can’t force her to not jump, so he offers her a night on the town. At the end of the night, after stealing a motorcycle, Deadpool drops Danielle off at hospital. She’s initially resistant to go in, but Deadpool admits she needs help; he’s just not the guy to do it. In an extremely tender moment, Deadpool provides the company and emotional support Danielle needs to check herself in.
12 SADISTIC: KILLED THE MARVEL UNIVERSE
Comic book characters exist within a multiverse, which means different versions of reality exist. Occasionally these changes are subtle, but sometimes they are massive. In one particular reality, Wade Wilson is institutionalized by his superhero colleagues. Unbeknownst to them, Psycho Man is the doctor overseeing Deadpool’s treatment and he wants to manipulate Deadpool into killing for him. Instead, Deadpool becomes more mentally unhinged and fully realizes he lives in a fictional world; one that ought to be destroyed. From there, he proceeds to kill every super-hero and super-villain in the Marvel Universe.
The series concluded with Deadpool understanding he’s a fictional character. However, he wants to find peace (and believe all fictional characters should too), and the only way to do that, according to him, is to kill the readers so the stories can end.
11 HEROIC: SACRIFICED HIMSELF TO END THE ZOMBIE APOCALYPSE
In Night of the Living Deadpool, Deadpool inadvertently played a part in bringing about the end of the world via a zombie apocalypse. Feeling responsible, Deadpool goes to the lab where the virus was born and ingests the zombie-making serum. Surrounded by zombies, Deadpool hopes his healing factor combined with the serum will transform the zombies back into humans. Unfortunately, instead of turning back into humans, the zombies are turned into Deadpool clones. This leads to the series Return of the Living Deadpool.
Wade survives his encounter with the zombies, but has little memory of what’s happened. He meets some survivors who inform him the world is overrun by Deadpools. Knowing that the Deadpools will kill all the remaining humans, Deadpool infects himself with a proper cure. This time, at the coast of his own life, Deadpool spreads the virus and kills 99% of the infected Deadpools.
10 SADISTIC: STARTED THE ZOMBIE APOCALYPSE
Wade Wilson loves chimichangas, or at least that’s what the Internet would have you believe. In fact, he’s more of fan of spouting the word, then actually eating them. Regardless, in Night of the Living Deadpool, Wade goes to his favorite chimichanga place and puts himself into a literal food coma. When he awakes, he is the only one in the restaurant.
Confused, Deadpool walks around the city until he discovers a discarded newspaper with a headline that reads: The Dead Walk! Deadpool realizes he slept through a zombie apocalypse. Heading out to find answers, Wade comes across an A.I.M. scientist who claims to have started the zombie plague by experimenting with Deadpool’s own healing factor. As a result, Deadpool, and the reader, are left feeling (probably rightly so) that Deadpool is responsible for the end of the world.
9 HEROIC: BECAME AN AVENGER
Joining the ranks of the Avengers, Earth’s Mightiest Heroes, is one of the greatest honors that can be bestowed on a superhero. It requires that bit of something that you simply have to possess. Captain America believed Deadpool had that special something. In the pages of Avengers #0, Wade Wilson officially became an Avenger. Thanks to Steve Rogers, he also got an Avengers ID card and full security clearance.
Not every hero on the team, especially Spider-Man, believed Deadpool had what it took to be an Avenger. While Deadpool acted indifferent to everyone’s spite, he was bothered, but ultimately, old man Steve Rogers admitted that he saw something in Wade that the mercenary rarely saw in himself: a hero. From there, Deadpool proved an invaluable asset while on the Avengers; he even saved the world once or twice.
8 SADISTIC: SHOT A BYSTANDER TO DISTRACT DAREDEVIL
With Deadpool acting like a wise-cracking, goof all the time, it’s easy to forget just how morally ambiguous he can be. Daredevil is the polar opposite of that. Daredevil is known for his straightedge, stern behavior, which was brought on by his religious beliefs and upbringing that oftentimes buries him in guilt. The two don’t get along.
When they crossed paths one time, it went about as well as you’d expect. Daredevil seemed to have beaten Deadpool, tying him up to hand him over to the authorities. Deadpool, knowing he had more pressing matter to attend to, was too clever to sit around idly and surrender. He figured to distract Daredevil by shooting an innocent bystander. This leaves Daredevil with a moral decision, save the bystander or arrest Deadpool. Needless to say, Deadpool escapes.
7 HEROIC: SAVED THE WORLD FROM UNDEAD PRESIDENTS
In 2013 Deadpool came face-to-face with past US presidents. After some of America’s greatest men are raised from the dead by a second tier necromancer, the undead presidents go on a rampage to save the country from its greatest threat: Americans. The idea of having heroes like Captain America, who are all about the US, having punch presidents in the face was a P.R. nightmare. The politicians and powers that be offered the job to Deadpool, since no one would question an amoral hero doing what he did best: causing chaos.
And so, one-by-one, Deadpool, proceeded to murder every undead President of the United States. From Honest Abe Lincoln to Teddy Roosevelt and George Washington, Deadpool fights them all. Though the battles begin to take an emotional toll on Deadpool and some of his friends are killed, Deadpool perseveres and sees the mission through, saving the world.
6 SADISTIC: KILLED THE MARVEL UNIVERSE (AGAIN)
Despite its grisly nature, Cullen Bunn’s Deadpool Kills The Marvel Universe was a resounding success. Followed by Deadpool Killustrated, the follow up tale, the final part of the trilogy was Deadpool Kills The Marvel Universe Again.
This time around, in yet another reality, Deadpool is being mind-controlled by the Red Skull and a group of supervillains. Yet even while he’s been killing his allies, Deadpool’s mind has been fighting the conditioning, letting him leave clues so his fellow superheroes can break the proverbial spell. They don’t. He kills the Avengers, the X-Men, every Spider-Man, the Punisher, the Guardians of the Galaxy, and loads of other heroes. It finally ends when Gwenpool snaps him out of it right before he murders her. After that, Deadpool goes on a quest to kill every supervillian on the planet.
5 HEROIC: TOOK A LASER BLAST INTENDED FOR A KID
Deadpool’s past action have a way of coming back to bite him in the butt, sometimes literally. This time around there’s a demon named Vetis who’s out to kill everyone’s favorite Merc With The Mouth. After getting tricked by Deadpool on multiple occasions, Vetis has returned with more power than ever before. Deadpool discovers he’s partly to blame for the demon’s power up, since it was Wade who killed a bunch of people and those people’s souls empowered Vetis.
As the two fight in the middle of the street, a kid is filming the battle on his phone. Vetis tries to murder the youngster, but Deadpool jumps in front of the blast, taking the brunt of the attack. It takes awhile, but Deadpool is finally able to finish off the demon Vetis once and for all.
4 SADISTIC: MURDERED MAJOR LITERARY CHARACTERS
After The Merc With the Mouth finished killing every superhero and villain in Deadpool Kills the Marvel Universe, the antihero moved on to loftier goals in Deadpool Killustrated. Deadpool convinces Man-Thing, the gatekeeper of an inter-dimensional portal that serves as a bridge between realities, to let him enter the portal. Man-Thing allows Deadpool to venture through and Deadpool takes advantage of the opportunity to continue his killing spree throughout other realities.
Amidst all the killing, Deadpool acknowledges that the only way to ensure that the heroes he’s killed stay dead is by assassinating the classic characters that the heroes are inspired by and modeled off. Deadpool then starts slaughtering major literary characters like Tom Sawyer, the Headless Horsemen, Little Women, Captain Nemo, etc. His insatiable bloodlust is so profound, Sherlock Holmes recruits a band of literary heroes to stop Deadpool. The greatest detective eventually sends Deadpool spiraling into limbo.
3 HEROIC: SAVED THE WORLD FROM THE RED SKULL
In Rick Remender’s Uncanny Avengers, the Red Skull steals the brain of the dead Charles Xavier and puts it in his own head. After learning to control his more violent tendencies, the Red Skull opts to take a subtle, rather than a grand, approach, in taking over the world. Making a home for himself in the Avengers Mansion, the Red Skull captured most of the Avengers Unity Squad and brainwashed them.
Unable to read or control Deadpool’s already fractured mind, Wade storms the proverbial castle, but the Skull has a mind-controlled Rogue beat him to near death. It was part of Deadpool’s plan however, as Rogue beating him allows the mercenary to get close enough to scoop Magneto’s helmet out of his duffle bag, put it on her head, and have her be immune to the Red Skull. From there, she’s able to defeat the Red Skull.
2 SADISTIC: KILLED AGENT PRESTON
After the emotional journey of "Secret Empire", Phil Coulson was still dead and buried, courtesy of Deadpool. Now that the world has been restored, there are some people who cannot let the inexcusable act go, chief among them Agent Preston, one of Deadpool’s closest friends. The deed hits closer to home for both Deadpool and Preston, since the latter is the surrogate mother of the former.
Preston’s mind, now inhabiting an LMD (Life Model Decoy), is as strong and durable as any android could hope to be. In Deadpool #33, she turns off her emotions and decides to make Deadpool pay for his crimes. She nearly succeeds too. Alas, the comic is called Deadpool and not Agent Preston, so Deadpool finagles a strategy to fight back and blows her up, killing one of the few people who ever genuinely cared about him.
1 HEROIC: GAVE HIS UNEMPLOYED FRIENDS WORK
Over the years there have been many mercenary-type anti-heroes that have fallen by the wayside, their unpopularity ensuring they were rarely seen. In Deadpool & The Mercs For Money, one of those anti-heroes, Solo, is using the identity of Deadpool to fight crime. Deadpool takes notice and thinks to start his own team. Recruiting a lot of old friends and heroes who are struggling even to pay rent, they become a team.
Granted, Deadpool’s motivation isn’t entirely selfless, as he is hoping to increase his popularity and make money by hiring himself and his team out to high bidders. Even so, his team is made up of Solo, Slapstick, Foolkiller, Terror Inc., and Stingray, all of who are considered D-listers. It was nice of Deadpool to at least try and make old and stale characters relevant again and give them a purpose.