Just to summarise my thoughts on Deadpool, You don't have to include it, this is just my opinion, but I strongly tie it towards the Revised Timeline because of various ties to the film series. This is just my own take, of course!
Connections
- Ryan Reynolds plays Wade Wilson.
- The X-Mansion is the same set from the Original Trilogy.
- Hugh Jackman is the Wolverine of the Deadpool films, appearing on a serial box, a poster in No Good Deed and in the after-credits scene of Deadpool 2.
- The Fox X-Men appear in Deadpool 2.
- The Essex Corporation owns the Orphanage in Deadpool 2 after a short reference in X-Men: Apocalypse that leads into Logan.
- Deadpool specifically references James McAvoy and Patrick Stewart as Professor X.
Contradictions
- Colossus seemingly can't change back to his organic form yet is seen in X-Men: Days of Future Past as a normal looking dude in 2023.
- Wade is seen killed by himself in a scene that looks like X-Men Origins: Wolverine. It should be noted that this doesn't mean X-Men Origins: Wolverine occurred, only a battle between "Wade" and James Howlett.
- Wade should be hitting 70 in modern day.
I don't count characters being born after 1973 as a contradiction.
Colossus
He was born after 1973, so his appearance and accent can be different easily. Pahaps his mutation developed naturally in the Revised Timeline and he was not altered by the Chernobyl incident as he was in the Original Timeline. He was likely raised in America in the Original Timeline, maintaining an American accent because of it.
On his appearance in X-Men: Days of Future Past, he can transform, he just doesn't want to. In Logan and Dark Phoenix, we see that the X-Men have become celebrities, which is also in Deadpool 2. Colossus is seen in the Logan comic in his metal form. Pahaps he does it to boost his ego and the overall public opinion of the X-Men, especially after Jean Grey killed a mutant icon. He could just like feeling strong. In 2023, however, he feels more confident, even maintaining a relationship with Kitty Pryde.
Deadpool('s?)
There are two options to explain the discrepancies here. Either the Deadpool from X-Men Origins: Wolverine is the same character or he isn't.
Same Character
In this scenario, Wade Wilson's powers were triggered in 1973 between the events of Trask's assassination and Striker's team assault in X-Men Origins: Wolverine in the Original Timeline, and he was never a proper mutant. Wade's mutant powers are random, and he was chosen for Weapon XI for this reason, having the potential for multiple powers at the same time.
In the Revised Timeline, using the Year of the Dog, we can place Deadpool in 1994-1996, Deadpool 2 in 1997 and No Good Deed in 1999. This is so that his age is consistent with the previous films. Technology and media simply evolved quicker, and films like Taken 2 and Blade: Trinity were released sooner. No Good Deed faces the potential problem of contradicting this, stating that Phone Booths disappeared in '98, but theres no reason it can't take place after Deadpool 2. This also explains the young X-Men, although Fox most likely considers them a recast instead of younger versions by Dark Phoenix. You could even say that that X-Men: Apocalypse Skye Fibre ad fits into canon because of this.
On Wade's murder of his previous self, pahaps Cable's time travel is similar to the Quantum Realm in that it allows you to travel to closely related universes, and he simply created another divergent timeline that spins off the events of X-Men Origins: Wolverine in another timeline.
Deadpool is the Son of Weapon XI?
In this scenario, Deadpool takes place in 2007-2009, No Good Deed in 2009 and Deadpool 2 in 2010, all based on the Year of the Dog.
Wade Wilson mentions his father leaving him when he was young. This could be because he was forced into becoming the Revised Timeline iteration of Weapon XI. While both Wade Wilson I and Wolverine had a fight, that doesn't prove that all of X-Men Origins: Wolverine occurred in the Revised Timeline or that the fight even happened during the Three Mile Island incident. It could have happened in 1979 before Logan was captured and seen in 1983 or after his escape in 1983. Wade goes back in time to kill his father who he hates.
This assumes that Cable's time travel is more controlled. Essentially, even though they stopped Russel from being a murderer, Cable's future still happened, only his family were never murdered. It blocks the butterfly effect while allowing specific changes. Further support of this is how Vanessa was saved yet Wade still forms X-Force to stop Russel and saves Peter, albeit with a different motive instead of Vanessa's death.
Of course, the upcoming The New Mutants is confirmed canonical too.