Following the news that there will be another Spider-Man trilogy starring Tom Holland, Marvel just got its perfect opportunity to introduce Deadpool to the MCU. On the advent of Spider-Man: No Way Home, which is set to debut in theaters in late December 2021, word got out that this will not be Tom Holland’s final film in the MCU. Indeed, there has been confirmation of not one more film, or two, but rather a whole new trilogy. This breaks the trend set by other MCU properties like Captain America and Iron Man, which were given three films each before concluding their story.
Meanwhile, Deadpool and its sequel Deadpool 2 were produced by 20th Century Fox, and were set outside of the MCU, due to the property's not belonging to Marvel Studios at the time. However, following the acquisition of Fox by Disney, Kevin Feige confirmed that the third Deadpool film will indeed see the wisecracking, fourth-wall-breaking superhero become part of the MCU. Now that more Spider-Man films are confirmed to be in the works, there’s no better movie for Marvel to introduce Ryan Reynolds' Wade Wilson to the MCU with than a future Spider-Man.
Deadpool and Spider-Man are no strangers to each other in the comics, and a recent crossover ran for fifty issues between 2016 and 2019. There are many similarities between the two superheroes, with both of their personalities prone to levity and jest being just the most obvious one. Both Spider-Man and Deadpool like to crack jokes, that’s for sure, but there is more to their pairing than that. Deadpool creator Rob Liefield even admitted that the design of his superhero took inspiration from Spider-Man’s costume. At points in the comics, Deadpool even pretended to be both Peter Parker and his alter ego Spider-Man on separate occasions.
How Deadpool’s bouts of breaking the fourth wall could function within the MCU is anyone’s guess for now, but Marvel Studios has played around with meta notions recently. WandaVision cast Even Peters as Quicksilver, who played the same character in Fox’s X-Men films. Even the upcoming Spider-Man: No Way Home has its fair share of meta aspects with Spider-Man villains from former films returning to give Peter Parker a hard time. It’s certainly possible for Deadpool’s penchant for the meta to work in the MCU, and it even seems that Marvel Studios is building up to it in recent times.
What direction Marvel Studios decide to take Tom Holland’s Spider-Man in the future is mere speculation at this point, but a team-up with Ryan Reynolds’ Deadpool would make perfect sense—and it could be quite easy to add Deadpool to the MCU. Funny enough, Ryan Reynolds himself has teased Spider-Man on Twitter during the production of Deadpool 2. There is definitely potential for Reynolds and Holland to riff off each other, were they ever to star alongside as their respective costumed personas, and considering Spider-Man and Deadpool are a fan-favorite pairing in the comics, a cinematic crossover is apt to deliver similarly intoxicating chemistry.