All 5 Deadpool Movies & Appearances in Order
As one of the most beloved Marvel antiheroes, Deadpool has been 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. Having said that, let’s take a look at all Deadpool movies and appearances so far.
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.
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.
5. Deadpool & Wolverine (2024)
Development on a third Deadpool film began at 20th Century Fox by November 2016, but was moved to Marvel Studios when Fox was acquired by Disney in March 2019.
The creative team had difficulty settling on a story until Jackman decided to reprise his role as Wolverine from Fox’s X-Men film series in August 2022. Several other actors from the X-Men films and other Marvel productions also returned as part of a multiverse story, which serves as a tribute to Fox’s Marvel films.
Deadpool & Wolverine is the first R-rated MCU film, retaining that rating from the prior Deadpool films. It grossed $1.338 billion worldwide, becoming the second-highest-grossing film of 2024, the highest-grossing R-rated film ever, and the 20th-highest-grossing film ever at the time of its release.
