Deadpool Movies in Order: Including X-Men Origins: Wolverine

Deadpool movies in order

Our favorite “Merc with the mouth”, Wade Wilson aka Deadpool, managed to gather quite the following considering he hasn’t been around for all that long like some other Marvel superheroes (or antiheroes to be more precise). Still, from the moment he appeared in X-Men: New Mutants, his persona was slowly evolving and growing in popularity. 

Nowadays Deadpool is almost a household name thanks to the movies. That can in part be attributed to the brilliant execution of the character by Ryan Reynolds. Deadpool movies are a perfect mix of juvenile humor, action, and cold brutality that remind us of Deadpool’s origins. 

In honor of Deadpool’s evolution, we decided to sit down and bring you a chronological list of all Deadpool movies in order of watching. So how many Deadpool movies are there? 

Deadpool Watch Order At A Glance

If you count Wade Wilson’s appearance in X-Men Origins: Wolverine, there are four movies on Deadpool’s movie list. The other three movies are his standalone movies and the only ones that are worth mentioning. The fourth movie on the list, Once Upon a Deadpool, is a re-cut PG-13 adapted version of the second Deadpool movie. Deadpool watch order is uncomplicated and to follow the story, the best Deadpool watch order is to simply view the movies in the order they were released in. 

  1. X-Men Origins: Wolverine (2009)
  2. Deadpool (2016)
  3. Deadpool 2 (2018)
  4. Once Upon a Deadpool (2018)

Deadpool Watch Order (Fully Explained)

1. X-Men Origins: Wolverine (2009)

X Men Origins Wolverine

X-Men Origins: Wolverine released in 2009 and directed by Gavin Hood featured Deadpool but he wasn’t the movie’s main focus. The story followed James Hawlet aka Wolverine (Hugh Jackman), his relationship with Victor Creed (Liev Schreiber), and his development in the context of Wiliam Stryker’s (Danny Huston) Team X. 

We also got to see how Wolverine got his adamantium claws and the tragic past that in part shaped his character. 

As mentioned before, Deadpool is not the movie’s main focus. He appears as a part of Stryker’s Team X along with fellow mutants Agent Zero (Daniel Henney), John Wraith (, Fred Dukes (Kevin Durand), and Chris Bradley (Dominic Monaghan). 

Team X, especially Victor Creed are known for the cold and brutal execution of their missions and have a complete disregard for human life. Considering Wade Wilson was a part of the group it’s not that much of a stretch. 

Wolverine left the group but the past came back to haunt him. Stryker and Agent Zero appear on his doorstep bearing news that Wade Wilson has been murdered and they heavily insinuate that Victor is responsible. 


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Until the end of the movie, we see Wade Wilson again though. He hasn’t been killed he has actually been enhanced and newly named “Weapon XI”, a movie equivalent of Deadpool. Wolverine fought him and managed to defeat him. But one thing that the movie got right is that Wade Wilson is not that easy to kill even by decapitation. The post-credit scene shows Wade Wilson crawling out of the debris and shushing the screen. 

Fans hated the Deadpool in this movie. Fox’s first take on Wade Wilson was poorly executed. And it would seem that Ryan Reynolds’ Green Lantern fiasco was repeating itself all over again. And this time it wasn’t about the CGI suit. It was poor execution of the character overall. But yes, one among many things that fans hated about the movie was the fact that Deadpool is not seen in his iconic suit. 

2. Deadpool (2016)

Deadpool 2016

Ryan Reynolds got his chance at redemption and he got to play Deadpool again. This time in his standalone movie. The first Deadpool movie released in 2016 and directed by Tim Miller, did everything right. It served as Deadpool’s origin story and introduction to his snarky, brutal but at the end of the day, extremely tortured persona. It managed to show Deadpool in a sympathetic light.

The first Deadpool movie was a success, people loved it. Especially the people who weren’t aware just how much Deadpool refuses to play by the rules and breaks the fourth wall. It was a refreshing change in the superhero genre that brought a bit of bloody and gory playfulness to the big screen. 

First Deadpool movie follows the origin story of a dishonorably discharged Special Forces operative Wade Wilson (Ryan Reynolds) at the start of the movie he is already working as a mercenary. He is in a committed relationship with a prostitute Vanessa (Morena Baccarin). Wade Wilson’s life turns into a nightmare when he gets diagnosed with terminal cancer. He leaves Vanessa in a fit of self-pity.

This is where the story really takes off since Wade Wilson is approached by Ajax (Ed Skrein). He offers him an experimental treatment that is supposed to rid his body of cancer and in the process even enhances it a bit. Wade Wilson has been subjected to the cruelest treatments, and almost none of them worked. Until he was subjected to treatment in a hypobaric chamber which brought him near the edge of asphyxiation periodically.

Hypobaric chamber managed to activate his latent mutant powers but left him horribly disfigured. Wade Wilson demanded that Ajax undo this to which Ajax only laughed. The upside was Wade Wilson was free of cancer and virtually indestructible, the downside was, that he managed to get horribly disfigured and piss off a group of powerful mutants. He eventually fought with Ajax and Ajax left him for dead in the burning laboratory.

To everyone’s surprise, Wade managed to survive this. He returned to his old life but was scared of showing his new ruined face to Vanessa. With his friend Weasel’s (T.J. Miller) help, Wade Wilson adopts his new vigilante persona “Deadpool” and decides to hunt down Ajax and his band of misfits.

3. Deadpool 2 (2018)

Deadpool 2 2018

Deadpool 2 was released in 2018 and directed by David Leitch. It was a bigger hit than the first movie and is regarded as the most successful spin-off in the X-Men film series. Deadpool 2 followed a simple albeit successful formula that the first movie established. It brought back the breaking of the fourth wall, borderline distasteful humor, and lots of gore. 

Deadpool 2 continues right back from where the first movie left off. Vanessa (Morena Baccarin) and Wade Wilson / Deadpool (Ryan Reynolds) are celebrating their anniversary and all is well and dandy until one of Wade’s missed targets breaks into his apartment and kills Vanessa. Deadpool is not able to cope with the death of Vanessa as he should, and he falls into a loop of self-pity and self-harm. He tries to take his own life multiple times but is not successful in his attempts due to the super-healing factor that saved his life in the previous movie. 


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He managed to get really close to dying and in his shock-induced state, he has a vision of Vanessa. Eventually, Colossus (Stefan Kapicic) recovers his body and brings him to the X-mansion. He talks Deadpool into joining X-Men and Deadpool agrees, because Vanessa would want him to. 

Now that he is part of the X-Men his new duties include responding to mutant-caused crises. 

One day he and Negasonic Teenage Warhead (Brianna Hildebrand) respond to a distress call that leads them to Russell Collins / Firefist (Julian Dennison). Firefist is being held at Mutant Re-education Center and is labeled as a problematic juvenile mutant. He causes a scene at the top of the building threatening to blow it up.

At first, Deadpool plays along and tries to stop the incident from escalating further, but then he realizes that Firefist was actually molested by the Center’s Headmaster. He kills the headmaster and all-around chaos breaks out. Colossus restrains both Deadpool and Firefist and they get arrested. 

They were eventually led to isolated supermax prison for mutants dubbed “Ice Box” and fitted with power-suppressing collars. While there, Deadpool realizes that he is getting weaker by the hour due to his power-suppressing collar.

His cancer starts to progress rapidly. In a way, he is relieved since this means that he will finally be able to die in peace. His plans are disrupted when Cable (Josh Brolin), a time-traveling cybernetic soldier attacks the Ice Box in his pursuit of Firefist. 

4. Once Upon A Deadpool (2018) 

Once Upon A Deadpool (2018) 

Since the initial release of Deadpool 2 was R rated and was a bit much for the younger audience, on December 21, 2018 a PG-13 re-cut version of Deadpool 2 was released. Once Upon A Deadpool features Deadpool as he retells the events from Deadpool 2 to Fred Savage. It was an attempt to parody the Princess Bride movie. 

New scenes were written by Rhett Reese and Paul Wernick, and David Leitch returned to direct them. 

Despite being a toned-down version of Deadpool 2 it still got a rating of 15 by the British Board of Film Classification. That same rating has been assigned to the original Deadpool 2 movie as well. 

Is Deadpool 3 out yet?

No, Deadpool 3 is not out yet but it has been confirmed that the sequel to Deadpool 2 will be incorporated into the Marvel Cinematic Universe under the careful guidance of Disney. Deadpool 3 has been confirmed multiple times at this stage with Ryan Reynolds getting back into the role of the titular character Deadpool. Back in 2021, Marvel Studios confirmed the R rating for the upcoming Deadpool 3. In March 2022, it was revealed that Free Guy’s Shawn Levy is the director of Deadpool 3 with Rhett Reese and Paul Wernick returning to write the script. 


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What movies should you watch before Deadpool?

Since Deadpool movies are X-Men film series spin-offs. A lot of fans are wondering whether there are some specific movies you should watch before taking on Deadpool. The answer is no, not really. Deadpool is a part of the X-Men universe and references it heavily, but the movies in themselves are somewhere on the continuity sidelines. Deadpool movies have a lot of jokes that reference X-Men Origins: Wolverine and Green Lantern so you should maybe watch those movies if you want to understand all the jokes.

And that’s it. We’ve covered Deadpool movies in order and hopefully, you will have fun watching them as much as we did!

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