Deadpool Movies in Order: Including All Appearances

As one of the most beloved Marvel antiheroes, Deadpool was adapted to many media. He appeared in various movies, video games, and animated series. Most of his recent fame has been attributed to the Deadpool standalone movies in which Ryan Reynolds starred as Deadpool masterfully.

Even though many works feature Deadpool, in today’s post, we’re going to focus on movies. Deadpools cinematic history is not as large as other Marvel names, but that will certainly change in the future. Having said that, let’s take a look at all Deadpool movies and appearances so far.

How many Deadpool movies are there?

There are only two Deadpool movies, three if you count Once Upon a Deadpool as a separate movie. In all of Deadpool’s appearances, he was featured in X-Men Origins: Wolverine, released in 2009. This brings us to a total of 4 appearances in live-action films.

However, his standalone movies received the biggest success. X-Men Origins: Wolverine was largely ignored since the version of the character that appeared there was not the same as that in his standalone movies.

Now that we’ve covered this, it’s time to check out all Deadpool movies in order, including appearances.

Deadpool movies in order (at a glance)

As we’ve mentioned before, Deadpools cinematic career started with X-Men Origins: Wolverine (2009). After that, he appeared in 2 standalone moves released in 2016 and 2018. Once Upon a Deadpool is a PG-13 re-cut of the movie released in 2018.

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

X-Men Origins: Wolverine was considered the worst character portrayal, but Reynolds managed to redeem himself with the two standalone movies. It was often commented how he was born to play Deadpool as the actor’s real personality somewhat matches that of Deadpool.

Are Deadpool movies connected?

Deadpool standalone movies are connected, but X-Men Origins: Wolverine movie is not connected to the Deadpool series. After the debacle that was the Wolverine movie, Deadpool received a reboot with a brand new origin story, one more similar to the comics. So no, Deadpool in the Wolverine movie is not the same one we’ve seen in the standalone movies; thus, those movies are connected.

Do you need to watch Deadpool movies in a specific order?

It would be best if you watched Deadpool movies in a specific order, which happens to be the release date order since the movies follow a strict chronological timeline and the second movie is closely tied to the first movie. X-Men Origins: Wolverine can be watched as a prequel to Deadpool 1 and 2 just so you can see all the differences between the versions of Deadpool and so you can witness the redemption of Ryan Reynolds.

What is the best way to watch Deadpool movies?

The best way to watch Deadpool movies is by release date order. Watch order of Deadpool movies is largely uncomplicated since the two movies are connected, and the second movie only continues Deadpool’s story established with the first movie.

Deadpool movies and appearances in release date order

1. X-Men Origins: Wolverine (2009)

We’re going to start our watch order of Deadpool movies with his first cinematic appearance, X-Men Origins: Wolverine. Deadpool wasn’t the main focus of this movie. The movie instead followed the origin story of James Howlet, aka Wolverine (Hugh Jackman). The movie featured Deadpool (Ryan Reynolds) in a smaller role in the context of “Team X.” Team X featured loads of other mutants like Agent Zero (Daniel Henney), John Wraith (will.i.am), Fred Dukes (Kevin Durand), and Chris Bradley (Dominic Monaghan).

The Wolverine movie was rather poorly received. Fox’s first take on Wade Wilson was poorly executed, and fans hated it. It was oddly reminiscent of Reynold’s previous fiasco with the Green Lantern movie. Luckily, he redeemed himself and erased Fox’s Deadpool with the first standalone movie Deadpool ever starred in 7 years later.

2. Deadpool (2016)

The first Deadpool standalone movie was directed by Tim Miller and featured the antihero in the main role. The movie was a wildly successful origin story of the character.

The movie begins with Wade Wilson working as a mercenary. He is a former Special Forces operative. Wade is in a committed relationship with a former prostitute Vanessa (Morena Baccarin). Wade is content and seemingly gets his life on track when he is diagnosed with terminal cancer. In his pursuit of a cure, he was approached by Ajax and offered to participate in experimental treatment. The experimental treatment turned out to be rather cruel and subjected Wade to inhuman suffering. It never managed to rid his body of cancer but did manage to trigger his latent mutant powers, an extreme healing factor albeit with a cost Wade was perhaps not willing to pay.

3. Deadpool 2 (2018)

Deadpool returned once again in the second installment in the series, this time directed by David Leitch. Once again, Ryan Reynolds stars as Deadpool and continues his life that was established during the first movie. Deadpool and Vanessa are planning their lives together, and on the night of their anniversary, one of Wade’s missed targets breaks into his apartment and kills Vanessa. This sets Deadpool on a self-inflicted path of vengeance filled with desperation. Self-pitty and, well, humor.

4. Once Upon A Deadpool (2018)

Once Upon A Deadpool is a re-cut PG-13 version of the original Deadpool 2 movie. The original movie was rated R, and this was an attempt to get a milder rating; it failed. Once Upon A Deadpool got the same rating as the original Deadpool 2. New scenes were added to the movie, and David Leitch returned to direct them.

The movie is an attempted parody of the Princess Bride movies. Deadpool retells the events of Deadpool 2 to Fred Savage, albeit with a milder approach to violence.

Where to watch Deadpool movies?

All Deadpool movies starting with X-Men Origins: Wolverine, can be watched on Disney+, the only exception is Once Upon a Deadpool, but you can find that movie on Amazon Prime Video.

Will there be more Deadpool movies?

There will be more Deadpool movies in the future. In fact, the third Deadpool movie is in development and will be officially a part of the MCU. Recently it was announced that Hugh Jackman will play Wolverine in the third installment, which greatly overjoyed the fans. Deadpool 3 is set to be released in September 2024.

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