Deadpool Movies in Order: The Complete Guide

Deadpool is one of the surprise hits in the superhero franchise movies, being ultra violent, hilariously funny, and featuring some of the best one liners. However it can be hard to know which Deadpool movie to watch first as there are a few of them now.

So let’s look at a watch order for the Deadpool franchise, so you know which movies to watch and in what order, so you don’t miss anything and get the most out of this R-rated series.

How Many Deadpool Movies Are There?

In total there are four Deadpool-featured movies, with his appearance in the 2009 X-Men film not being focused on him. The best Deadpool watch order is to go by their release date as this makes chronological sense in terms of the story. 

• X-Men Origins: Wolverine (2009)
• Deadpool (2016)
• Deadpool 2 (2018)
• Once Upon a Deadpool (2018)

Deadpool Watch Order (Fully Explained)

X-Men Origins: Wolverine (2009)

This film isn’t specifically focused on Deadpool as it follows Wolverine and his trials and tribulations coming up. Deadpool as a character was heavily criticized and Ryan Reynolds in particular was panned, although he did get a second chance to prove everyone wrong.

The tragic past that made Wolverine who he is is the main driver of the narrative, and we also got to see how Wolverine got his adamantium claws.

Deadpool appears as a part of Stryker’s Team X along with Agent Zero, John Wraith, Fred Dukes, and Chris Bradley.

Team X is a ruthless organization, and Deadpool is not quite Deadpool quite yet, but a mercenary Wade Wilson who shows his disregard for human life, which eventually turns Wolverine off the group.

However after he left, Stryker and Agent Zero reappear on his doorstep with the news that Wade Wilson has been murdered by another member, Victor.

Wolverine finds out that Wilson is not quite dead, but is now an enhanced version of himself, putting up quite the fight. After Wolverine separates him from his head, he believes the chapter to be over but we see Wade Wilson survive, telling the audience to be quiet.

Deadpool (2016)

The breakout performance that really brought the full depth and complexity of Deadpool to mainstream audiences, the film was made as a standalone focus on Deadpool, tracking his origin story.

Made on a $58 million budget but close to pulling in a billion in sales, it is incredible to think that the movie almost didn’t get made, as its high violence and other factors led to it getting a restricted 18 plus rating.

The constant fourth wall breaking by directly talking to the audience, the many different approaches to try and make a unique movie certainly helped with making the movie a success.

Reynold’s performance was lauded, with it now hard to imagine anyone else being able to pull off such a masterful comedic performance combined with slick action.

After Wade Wilson is dishonorably discharged from the special forces, he gets the gut punch that he has terminal cancer, and leaves his girlfriend immediately. After getting approached by a scientist offering him a miracle cure, he takes it only to end up as a mutant.

The treatment was brutal, with high levels of stress needed to awaken latent mutant genes, and the scientists resort to torture to provoke this response, but made a mistake by doing it to a guy who is never been shy from seeking revenge and doesn’t forget easily.

There are several side effects, including him becoming horribly disfigured, but the upside is that his cancer is effectively cured, he becomes seemingly unkillable and then realizes that his quest for revenge against the scientists that did this to him is the only thing left to do.

He starts going through and killing them one by one, showing little mercy towards those that have wronged him.

About 10% of the budget was cut right before production, with the hilarious outcome being that a planned gun battle near the end was cut completely.

The explanation in the film is that Deadpool forgets his gun bag in the cab on the way to the final battle, leaving him without his main weapons but that doesn’t seem to faze him that much.

Other changes were that the villain Ajax’s goons were slimmed down to just be Angel Dust, played by former UFC fighter Gina Carano and a big motorcycle chase sequence between Deadpool and Ajax was removed.

Deadpool 2 (2018)

After his girlfriend Vanessa is killed after they went after Deadpool but missed, Deadpool realizes he has nothing else to live for. Unfortunately for him, due to his super healing powers he can’t kill himself, despite trying many times.

Being rescued by one of the X-Men, Colossus (who Deadpool was unable to defeat in the first Deadpool film) he gets brought to the X-mansion, being convinced of their goals but basically only joining because of a vision he saw of Vanessa that urged him to. 

Finding purpose in helping out in mutant-caused crises, he comes across Firefist and helps him out after realizing he has gone through abuse similar to how Wilson was abused in times of vulnerability.

After making a decision to kill the abuser but only killing a staff member, Deadpool is prevented from further destruction by Colossus who restrains both Deadpool and Firefist, leading to them getting arrested. 

Deadpool is then put in a specially-made prison for mutants and made to wear a power-suppressing collar, being convicted of murder and not getting a pass for it just because he is now a mutant.

This has the unfortunate side effect of stopping Deadpool’s healing factor, and as his cancer is still in the body but repressed by the constant healing, this means Deadpool is facing death.

Deadpool accepts death, given that he feels he has nothing to live for, only for the time-traveling soldier Cable turning up, destroying the prison in an attempt to get at Firefist.

After some failed attempts, they get free but the continued presence of Cable sees Firefist keen to get out of the prison, enlisting the help of Juggernaut who conveniently rips Deadpool in half on the way out.

It turns out that Firefist’s rage turns him into a serial killer in the future, forcing Cable to work alongside Deadpool to save his own family, and Cable uses his time travelling device to save Deadpool’s life after he dives in front of a shot from Cable at Firefist.

This sacrifice by Deadpool changes the future, meaning Firefist changes his ways and not becoming a serial killer or immolating Cable’s family, only to be accidentally killed by Deadpool’s friend soon after.

Being one of the highest grossing films of the year, it is an amazing followup to the 2016 film.

Once Upon a Deadpool (2018)

Due to the rating of the previous two films, it was hard for them to reach a wider audience, especially among the younger demographic, which is a big one for superhero franchises. A less violent version of the film was released in 2018, although still limited to teenagers.

The movie is retold in the theme of the classic film The Princess Bride, with many gory details removed to make it easier to get past the ratings classifications.

Deadpool kidnaps his ‘buddy’ Fred Savage and ties him to a bed, making him listen to a retelling of Deadpool 2.

There are some major differences that come via comments from the pair. For example, when Juggernaut rips Deadpool in half, they jest that the legs may grow a new Deadpool. 

Savage also mentions how Brad Pitt got a cameo in the role of Vanisher, and Deadpool mentions that he has both Celine Dion and Matt Damon in his basement as he admires them as performers so much.

Playing off the steady appearances during both the credits and post-credit scenes, Deadpool goes very meta and discusses how they love post-credit scenes, all the while playing the original scenes from Deadpool 2.

After keeping Savage tied down for three days to get through Deadpool 2, Savage has trouble walking after being untied. Deadpool shows his eclectic personality by helping him to walk.

Related Movies You Should You Watch Before Deadpool

While Deadpool is a part of the X-Men universe, there isn’t anything specific you need to watch to get a feel or understand key points of the Deadpool storyline.

You could even skip X-Men Origins, as the Deadpool that is featured in there is quite different from the 2016 release, and the reimagining of the Deadpool character is fully self-contained from the 2016 version, and in my opinion is the much better depiction.

There are some in-jokes and references to X-Men Origins: Wolverine and Green Lantern, due to Reynolds being in both of them sprinkled throughout the Deadpool movies.

So if you want to understand all the jokes you could give them a watch, but neither are particularly good movies, with Green Lantern in particular getting bad reviews and not being his best work.