All 10 X-Men Movies In The Order You Must Watch Them
2. Deadpool (2016)
As of right now, Deadpool is the furthest point in the new X-Men timeline. As far as when it takes place exactly is unclear. The only real indicator is that smartphones and Twitter exist at this point. This movie has to be placed in the new timeline due to previously seeing a different story play out for Deadpool in the '80s. There's also a redesigned Colossus that looks different from other iterations, one that apparently spent more time in Russia than the original timeline.
There's only one way Deadpool works with the timeline we have, and that's taking some liberties with his age. This is still the same Wade Wilson that we saw in X-Men Origins: Wolverine, but in this new split timeline, he never made it to the Weapon X program.
So that would make the Deadpool that was in Origins probably in his late teens or early 20s and in his solo movie in his late 40s or early 50s. Yeah, it's a stretch, but it's the only way these movies could exist in the same universe.
Given the kind of character Deadpool is, his movie is concerned the least with trying to make sense of the X-Men continuity, even going as far as to call it out for being confusing.