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12 Best Deadpool And Wolverine Moments In Comic Book History

Always on brand, Ryan Reynolds recently released an unorthodox announcement confirming that Hugh Jackman will co-star in the upcoming "Deadpool 3." Reprising a 22-year-old role, Jackman will suit up as Wolverine for one last throwdown with Marvel's most obnoxiously lovable mercenary. Reynolds and Jackman have shared an ongoing social media sparring session often centered around their most popular characters. Regardless of the film's origin story, fans cannot wait to see the regenerating degenerate face off against the original Weapon X under the Marvel Cinematic Universe banner.

With comparable origin stories and polarizing personalities, Deadpool and Wolverine are the perfect comic book pairing. The Merc with a Mouth has a way of getting under the skin of everyone's favorite grumpy Canadian — and it usually ends with one of them losing a body part. Conversely, these two hardened heroes often find themselves on the same side of the fight, sharing friends and foes alike. With both Marvel products becoming iconic in the comic book industry, it is always a treat when they clash for a crossover. So, before Logan and Wade Wilson meet up in the MCU — in what is certain to be a tentpole event — keep reading to discover some of the best moments the characters have shared in their source material throughout the years.

First appearance together - Wolverine #88 (1994)

Wolverine first clawed his way into comic book panels in 1974 when he gave the monstrous Hulk a run for his money. After an ambiguous introduction, it was his arrival in 1975's "Giant-Size X-Men" when the character truly began slicing things up. Quickly becoming a fan favorite, the claw-fisted Canuck bounced around the Marvel universe, becoming a member of superhero teams like Alpha Flight, the New Fantastic Four, and The Avengers, all while retaining a regular spot on the X-Men roster. It is no surprise that Wolverine has become a regular contender in the debate of the most popular comic book characters of all time.

Meanwhile, Deadpool is a relatively new character, as far as comic book icons are concerned, with his debut coming in issue 98 of "The New Mutants" in 1991. With his fourth-wall-breaking humor and regenerating super abilities, Deadpool had a meteoric rise in popularity, becoming one of the most beloved characters in comic books.

Despite the massive popularity of these masked warriors, it took some time for Marvel to clash their blades. Deadpool had already become a thorn in the side of many characters before arriving in issue 88 of "Wolverine." Sharing a similar backstory, Wolverine and Deadpool crash into one another as they look for a third character presenting himself as Weapon X. With Logan's healing powers weakened, the mercenary got the best of their first fight, impaling his combatant with two swords.

Sparring buddies - Deadpool #27 (1999)

It's evident from the first introduction that Deadpool is a little off the wall. Nevertheless, there was a time when the mercenary's personality went beyond eccentric into unstable territory. In the late 1990s, Deadpool received a new regular writer in Daniel Way, who took the character in a new direction by diagnosing him with schizophrenia. Although a hotly debated choice for the character, the story developed into Wade seeing hallucinations, which the audience could observe via an illustration tool dubbed "Pool-O-Vision."

Over the series, Deadpool's condition worsened, leading to him reaching out for psychiatric assistance. During one of his therapy sessions, the character decides that he does his best thinking while focused on a fight — and there is no better combatant for an extended throwdown than the regenerative-powered Wolverine. Unfortunately, by the time the mercenary catches up with Wolverine in "Deadpool" #27, the Canuck is in no mood for a brawl — until Wade knocks out Logan's good friend Kitty Pryde.

Wolverine and Deadpool vs werewolves - Wolverine Annual (1999)

In just their 4th comic book meeting, Deadpool and Wolverine finally join forces to battle a common enemy. Arguably, the two powerhouses were on the same side when Wolverine saved Deadpool from a rebounded Weapon X project back in "Wolverine Annual '95." That story centered more around the relationship between Wolverine and his old ally Maverick, while Deadpool makes a quick exit after being rescued. However, when Wolverine crossed paths with Wade Wilson again in the giant-sized "Wolverine Annual '99," it was a much more unique endeavor.

On the cover, the "Wolverine Annual" is pinned as a "grudge match" between the two masked vigilantes, and truthfully it begins with Logan getting some hits in as revenge for what Deadpool did to Kitty Pryde in their last crossover. Unfortunately, their battle does not last long, as they find themselves entwined in the matters of the Council of Werewolves. Upon wrapping up the unexpected interruption, Deadpool and Wolverine put their differences aside and grab a beer together — but not before Logan gets one more satisfying punch in.

Wolverine beheads Deadpool - Cable and Deadpool #43 and 44 (2004)

As exciting as Deadpool-Wolverine comics can be, the Crimson Comedian has had more significant partnerships throughout his comic career. He shared a title with everyone's favorite web-slinger for 50 issues in "Spider-Man/Deadpool" between 2016 and 2019. Even more famous is Deadpool's relationship with the time-traveling X-Man Cable, which was at the center of the character's last feature film, "Deadpool 2." Before splitting the big screen, Deadpool and Cable had been shooting bullets at each other for years, which makes sense considering they were both introduced under the same title and share a creator in Rob Liefeld. But with the two gun-touting antiheroes leading their own series, and both tightly linked to X-Men lore, it was only a matter of time before Wolverine came to spoil the party.

By issue 43 of "Cable and Deadpool," Cable had temporarily broken off from his partner, leaving Wade Wilson to his own adventure. Of course, the Merc gets up to no good, as his good friend Weasel is being heralded as the new leader of the terrorist group HYDRA. Meanwhile, Wolverine has taken it upon himself to take out the extremists, leading to him clashing with his old enemy. No time for catching up, Logan cuts off Deadpool's head in the final panels, leading to an all-out brawl in the next issue that features a cover with Cable's name crossed out, replacing the standard title with "Wolverine and Deadpool."

Deadpool the Hunter – Wolverine: Origins (2006)

Wolverine and Deadpool are closely linked in the comic books because they are both experiments of the Weapon X project. This shared backstory was the manufacturing of Deadpool's creator Rob Liefeld, who said in a Forbes interview, "Wolverine was my guy. If I could tie anything into Wolverine, I was winning." Thankfully, with Logan being centuries old and linked to various parts of the Marvel universe, making connections is easy. Due to the character's traumas and difficulties, Wolverine has spent much of his career attempting to recover his memory. This hunt for the truth led to writer Daniel Way releasing the 50-issue collection "Wolverine: Origin."

The Merc with a Mouth arrives in "Wolverine: Origin" issue 21, after taking on a significant bounty to kill Wolverine. Stringing his opponent on through multiple issues and panels with a series of tricks and gags, which include exploding babies and dropping a piano on Logan's head, Deadpool finally captures his prey. But before Wade can finish the job, he is interrupted by Wolverine's son Daken, who has a staked claim of killing his father. While the story goes on to be a Daken-Wolverine matchup, the run is one of the most remarkable illustrations of Deadpool and Wolverine's ongoing rivalry, with both fighting to the point of unconsciousness.

Joining the same X-team - Uncanny X-Force (2010)

Despite Wolverine and Deadpool having deep ties to the X-Men and their multiple derivatives, it wasn't until 2010 that the two would share uniforms. Thankfully, it was worth the wait, as writer Rick Remender delivered one of the most memorable X-rosters in comic history with "Uncanny X-Force." Paying service to the audience, this offshoot X-team featured a lineup of fan-favorite characters, including Archangel, Psylocke, Fantomex, and a powerful "Age of Apocalypse" variant of Nightcrawler.

Deadpool and Wolverine remain integral members of the team throughout the complete 35-issue run, helping Archangel uphold his oath to defeat a new clone of Apocalypse — until the flying mutant is revealed to be the true villain. Regardless, as teammates, the berserker and the mercenary manage to slice their way through powerful enemies, including Dark Beast, the Brotherhood of Mutants, and the Omega Clan. Unfortunately, the short-lived series ended in 2012, closing out the only X-team to feature Wolverine and Deadpool simultaneously and taking away their stylish grey and black variant costumes.

Deadpool does drag - Wolverine/Deadpool: The Decoy (2011)

Surprisingly, despite these characters' extended print history, Wolverine and Deadpool only shared a title one time: a one-shot comic titled "Wolverine/Deadpool: The Decoy." In the United Kingdom, there is an ongoing title, "Wolverine and Deadpool," but the books are collected reprintings of the respective characters' individual popular stories. Meanwhile, there are rumors that the pair may reunite for a title in the near future. Still, as it stands, if you want a crossover title with the berserker from the Canadian wilderness and the wildcard Wade Wilson, there is but one book to pull off the shelf.

The official synopsis for "The Decoy" promises "the most cheerful Weapon X reunion since, well, since Weapon X turned James Howlett and Wade Wilson into super-killers." Thankfully, the story does not disappoint when Logan enlists his old nemesis to fight a giant robot. The only catch? Deadpool is going to have to get dressed up for the occasion. The target is a Shi'ar automaton programmed to hunt and destroy Wolverine's unrequited love interest Jean Grey, but unfortunately, Jean isn't around anymore. Thankfully, Wade Wilson is brave enough to dress the part and become the perfect bait.

Deadpool kills Wolverine - Deadpool Kills the Marvel Universe (2012)

In one of Marvel's most outlandish and exciting stories of our generation, Deadpool goes on a complete rampage in what is appropriately titled "Deadpool Kills the Marvel Universe." The story, which takes place in an alternate universe, starts with Wade Wilson being forced into an asylum by the X-Men in hopes of curing his mental disabilities. However, a brainwashing attempt by his doctor goes haywire, sending Deadpool over the deep end and starting one of the bloodiest comic titles in the Marvel library.

Without mercy, the unhinged Wade Wilson slices his way through the Fantastic Four and The Avengers before turning his sword on the X-Men in the third issue. Tying Professor X to a chair, he forces the X-mentor to watch as his beloved team falls victim to Deadpool's deadly maze. However, when the panels turn to Wolverine, Deadpool decides to do the job by hand. Using a sword of carbonadium, a fictional element that dilutes Wolverine's healing ability, Deadpool decapitates his long-time nemesis, declaring that his popularity will not save him this time. The mini-series ends in the next issue when Deadpool finds and kills the writers of the comic as they plot out the conclusion.

Destroying North Korea together – Deadpool: The Good, the Bad, and the Ugly (2013)

Wolverine and Deadpool have wretched reputations across the Marvel universe. Regardless, both characters share a mutual respect for the comic company's golden boy, Captain America. While their methods may clash, these three icons share the unique bond of all being experimented on by unethical government projects. This connection is at the center of the trio's team-up when Deadpool discovers one of his former torturers is still operating in North Korea.

Appropriately titled, given Deadpool's respect for Cap and hardened relationship with Logan, "The Good, the Bad, and the Ugly" collects a run of "Deadpool" comics later printed as a collected edition. Wade, Logan, and Steve find themselves in a tumultuous situation in North Korea when they discover the local government has been using Deadpool's DNA to clone their own mutilated versions of the X-Men. Teaming up with the disfigured clones, the trio not only defeat their enemy but blow the whole place to smithereens. This small, unsuspecting story goes beyond binding three definitive comic characters, and has become one of the most celebrated Deadpool titles of all time.

Marvel's biggest event reimagined with Deadpool - Deadpool's Secret Secret Wars (2015)

Long before the Marvel Cinematic Universe exploded minds by bringing its heroes together into ambitious crossover events, the comic book world paved the way. One of the first titles to bring Marvel's most-popular properties together was "Secret Wars," published between 1984 and 1985. Collecting a slew of the company's greatest heroes and villains, the story became the blueprint for building massive crossover events that have become a tradition for comic publishers. "Secret Wars" is one of the most important moments in comic book history and is set to be the basis of an upcoming "Avengers" sequel.

What most fans don't know about "Secret Wars" is that Deadpool was an integral part of the story, despite not being created for another seven years. "Deadpool's Secret Secret Wars" reveals how the mercenary fought alongside Wolverine, the X-Men, Fantastic Four, The Avengers, and Spider-Man in the Beyonder's game between good and evil. Hilariously, the only reason nobody remembers that Deadpool was involved is that Wasp was so ashamed of hooking up with him during the event that she effectively made everyone forget that he was even there.

Deadpool spoils the X-Men's fancy party - X-Force #20 (2021)

In 2021, the X-Men hosted a night of high fashion and elegance with the "Hellfire Gala." The event commemorated the mutant region of Krakoa opening its gates to the non-mutants of the world. A celebration of mutant culture, all the big names were invited, including The Avengers, Fantastic Four, every X-faction, and even Jon Hamm. Expanding across every X-title, the highlight of the evening is the announcement of the new X-Men roster as voted by real-world comic book readers.

Of course, when it comes to a significant superhero party, there are some who will want to crash the party, leaving others to play guard duty. In the case of "X-Force" issue 20, Deadpool takes the role of spoiler, while Wolverine is the bouncer ready to send him packing. Insulted that he didn't receive an invite to the mutants' big shindig, the mercenary attempts to break in. Unfortunately, Wade is not an official mutant — no matter what he tells you — and Wolverine has no problem being the party-pooper. Deadpool gains the upper hand during this round, shooting Logan point-blank in the face, but he still has plenty of backup at the all-star X-event.

Poolverine monster - Wolverine #23 (2022)

Finally, we reach Wolverine and Deadpool's latest comic book outing — though the publisher is sure to ramp up their crossovers leading to their cinematic event. The pair have collided for over two decades, spanning significant moments in their backstory and the larger Marvel universe. More often than not, Wolverine and Deadpool use their parallel healing abilities to combat each other for some of the most violent panels available. More recently, the duo has established mutual respect, and even when they don't agree, they are not as determined to finish one another off.

Set on reinstating his membership card and becoming a member of X-Force once again, Deadpool goes to his old friend, hoping to hash out their differences. Taking a spin at the Danger Room together, they find the battle simulation has become more dangerous than they bargained for. After being sliced to bits by far too many buzzsaws, both heroes' healing factors come into effect. Unfortunately, with their parts strewn across the room, their bodies blend together for one of the more disturbing character-combinations Marvel has delivered. Thankfully, the Cronenberg-style mashup is only temporary, and after sharing bodies, Wolverine gives Deadpool the job.