A Timeline of the Deadpool-Wolverine Partnership

We break down a full timeline of Deadpool and Wolverine's relationship ahead of 'Deadpool & Wolverine.'

Deadpool and Wolverine characters side by side with text "A Timeline of Deadpool & Wolverine"
Complex Original
Deadpool and Wolverine characters side by side with text "A Timeline of Deadpool & Wolverine"

It’s been 30 long years coming. There have been extreme highs and lows in the journey to get here but, on July 26, Deadpool and Wolverine will finally join forces to (hopefully) set the MCU straight. After years of back-and-forth verbal taunts, dares, and outright demands between Ryan Reynolds and Hugh Jackman, Disney gathered the relevant Infinity Stones of ownership rights to set the stage for Deadpool & Wolverine, in what could be the biggest Marvel Universe event since The Infinity Saga. 

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The First Appearance of Wolverine: The Incredible Hulk #180 (Oct. 1974)

Wolverine first popped up in Marvel Comics in The Incredible Hulk series as an agent of the Canadian government. He technically only appeared in the final panel of issue #180, but was given the full-book treatment in the following issue. Codenamed “Weapon X,” Wolverine was deployed by the powers that be Up North to deal with a rampaging Incredible Hulk. Inserting himself in a battle between Hulk and Wendigo, Wolverine didn’t waste any time making an impact, challenging two behemoths who towered over him. As we all know, Wolverine would leave the Canadian government behind and become an integral member of the X-men.

The First Appearance of Deadpool: The New Mutants #98 (Feb. 10, 1991)

In his first appearance, Deadpool is a mercenary hired by the time-traveling badass Cable to take out the New Mutants lead. After popping up a few more times to take on foes such as The Avengers and The Punisher, Deadpool started to gather a strong fanbase, which eventually led to his own mini-series in 1993 and resulted in his own ongoing title in 1997. Ever since then, the mercenary who won’t shut up has crossed blades with practically every member of the MCU.

Wolverine and Deadpool First Meet: Wolverine #88 (Dec. 1, 1994)

In their first on-page encounter, we find Deadpool trashing the apartment of an ex-girlfriend after failing to win her back from her new boyfriend, Garrison Kane.  After Deadpool threatens Kane and Deadpool’s ex, Wolverine (who happens to be Kane’s buddy) enters the fray. What ensues is a stab-fest of a battle where Logan and Wade’s healing powers are put to the test.

Deadpool Challenges Wolverine: Deadpool #27 (Feb. 24, 1999)

Suffering from hallucinations, Deadpool comes to realize that the one thing that reduces them is when he is battling other superhuman opponents. In order to remedy his conditions, Deadpool flies to Japan, where Wolverine is staying, to challenge him to a fight. Wolverine initially refuses, but after Deadpool strikes Logan’s longtime friend Kitty Pryde, Wade finally gets the battle he wanted.

Another Epic Deadpool-Wolverine Battle: Wolverine Annual #1 (Mar. 11, 1999)

Deadpool is hired to execute a famous writer named Duncan Vess. Coincidentally, Wolverine is at a Vess book signing to procure a signed copy for Kitty Pryde. Wolverine picks up a familiar scent and realizes that Deadpool is in attendance and rushes to find him. What ensues is another epic battle between two unstoppable entities—plus a werewolf is thrown in for good measure. This battle actually ends with Wolverine and Deadpool gaining mutual respect for each other and going off drinking together.

Deadpool and Wolverine’s Bloodiest Battle Yet: Wolverine Origins #21 (Feb. 20, 2008)

Wolverine’s origin story was fleshed out considerably in the Wolverine Origins comic run. In this five-part epic throwdown, Wolverine and Deadpool have what is considered to be their most violent encounter. Deadpool has been hired to kill Wolverine (a tale as old as time) by setting off a bomb directly in front of him.  Limbs are lost, bullets travel where they’re not supposed to, and an entire city is almost taken out. 

Deadpool Encounters Wolverine in Animated Form: Hulk vs. Wolverine (Jan. 27, 2009)

In the hit straight-to-DVD animated film, loosely based on the first appearance of Wolverine, Weapon X is tasked by Department H of the Canadian government to track down the Hulk, who’s been causing a ruckus in the Canadian wilderness. After a back-and-forth battle between the two, they are both subdued by numerous tranquilizers shot by Team X, consisting of Wolverine mainstays Omega Red, Lady Deathstrike, Sabertooth, and you guessed it, Deadpool. Wolverine and Hulk eventually team up to escape capture by Team X.

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Wolverine and Deadpool First Appear Together in Live-Action: X-Men Origins: Wolverine (May 1, 2009)

In the first of what was supposed to be a series of X-Men origin stories focusing on one mutant at a time, the initial installment was the origin story of Wolverine. The plot of the movie focuses on the shared history of Sabertooth and Wolverine, and how Logan was inducted into the Weapon X program and had his skeleton bonded with the indestructible metal adamantium. Also touched on is Team X, the government task force that Wolverine and Sabertooth work for under William Stryker. On that team is a young Wade Wilson, played by Ryan Reynolds before his Deadpool transformation. The movie was a critical disaster due to its cliché writing and subpar special effects. But what many consider the biggest travesty of all was what became of the first live-action interpretation of Deadpool. Instead of being the Merc with the Mouth we all know and love, Reynolds was shaved completely hairless, given an assortment of powers the character never had in the first place, and—worst of all—had his mouth fused shut. Basically this depiction was everything that the character wasn’t, and the fans, as well as Reynolds, loathed the movie as a result.  

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First Appearance of Uncanny X-Force: Uncanny X-Force #1 (Oct. 2010)

Meanwhile, in the comics world, the first edition of the Uncanny X-Force premiered a new superhuman team consisting of Psylocke, Archangel, Fantomex, Deadpool, and Wolverine.  As a spinoff of the X-Men, this was a darker iteration of the team where each member had one thing in common: They had each taken a life.

Wolverine Is Teased in Deadpool’s First Movie: Deadpool (Feb. 12, 2016)

After the critical failure of X-Men Origins: Wolverine, doing justice to the character of Deadpool became a passion project for Ryan Reynolds. There was initially a Deadpool movie in pre-production before Origins was released, but after that unsuccessful interpretation, Reynolds and his team chose to adapt the character more faithfully for his own movie. As a result, we were given the correct portrayal of Deadpool, with lots of violence, cursing, and plenty of fourth-wall breaking. The Wolverine tease occurs when Deadpool unmasks near the end of the film to reveal a picture of Hugh Jackman over his scarred face.

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Hugh Jackman Initial Last Appearance as Wolverine: Logan (Mar. 3, 2017)

In what was supposed to be the last time Hugh Jackman donned the claws, we were given the incredible James Mangold project that was Logan. Taking place in the not-too-distant future, an older, beaten-up Wolverine is tasked with one last mission to save a younger female clone of himself.

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Deadpool Cleans Up His Past : Deadpool 2 (May 18, 2018)

In his second live-action romp, Ryan Reynolds doubles down on the Hugh Jackman shots to seemingly goad him into portraying Wolverine once again. He even begins the movie by exclaiming “F*** Wolverine” in response to him having to top the character’s powerful death scene (at the end of Logan—c’mon, it’s not a spoiler, that movie came out in 2017). And of course, how could we forget the epic ending where Deadpool uses a time machine to go back and fix the errors of his past, including killing the “other” Deadpool from X-Men: Origins, not to mention shooting himself before he accepts the role of Green Lantern. That’s meta humor baby!

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Ryan Reynolds Announces He’s Bringing Hugh Jackman Out of Retirement: YouTube Video (Sept. 27, 2022)

Now this was the moment that sent the MCU fanbase into pure giddiness. In 2022, Ryan Reynolds released a video apologizing for missing that year’s D23, but for good cause: He was working on Deadpool 3, a film whose future was put in doubt due to the character’s rights belonging to Disney now. The question of whether or not Disney would let Reynolds’ Deadpool be as raw and uncut as the previous two movies was answered, and that answer was a resounding YES!  And to top it off, after Reynolds talks about hitting a wall in the creative process, we see a person who appears to be Hugh Jackman walking around behind him, slightly out of focus. Ryan asks, “Hey Hugh, wanna play Wolverine one more time?” Hugh answers: “Yeah…sure, Ryan.” And the countdown to July 2024 officially began.

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