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Deadpool
Deadpool 2
This is just for general info on the character’s backstory and to know who the people at Wades’s birthday party are, although Deadpool 2 is also referenced explicitly in relation to his time jumping and the fate of the X-Force.
Logan
The end of Logan is heavily referenced throughout the film and this is where we first meet Dafne Keen’s X-23.
X-Men
Several of the X-Men characters are mentioned; Charles, Scott, Jean, Magneto. Tyler Mane and Ray Park reprise their roles as Sabretooth and Toad, and there is a line in this first X-Men movie about the yellow suit Wolverine wears in this film.
X-Men 2
Lady Deathstryke from X-Men 2 is in the Void. This is also the film that introduced Pyro.
X-Men Origins: Wolverine
This was the first film in which Ryan Reynolds played a version of Deadpool which is shown in flashback. It also the movie that best lays out the relationship between Wolverine and Sabretooth.
X-Men: The Last Stand
This is the film that first has Juggernaut and his magic helmet in it. Vinnie Jones clearly didn’t want to come back but multiverse multiverse blah blah blah.
X-Men: First Class
Azazel from this movie is also part of Cassandra Nova’s crew.
Daredevil
Elektra
Jennifer Garner’s Elektra is from these two movies and Daredevil is mentioned.
Iron Man
Iron Man 2
You need to have seen both of these films to understand Happy Hogan’s career development. The Captain America Shield from Iron Man 2 is in his office as well.
Antman & The Wasp
This is where we properly learn about Antman’s ability to become a giant, although we first see it in Captain America: Civil War.
Blade
Blade: Trinity
Blade is in this film and the first of his movies is where the line about ice skating uphill comes from. You need to know that Ryan Reynolds was in Blade: Trinity too and that he and Wesley Snipes apparently did not get on. ‘I don’t like you.’ says Blade to Deadpool. ‘You never did.’ he replies.
The Greatest Showman
The opening bars of two songs from Hugh Jackman’s famous musical play on the radio in the Honda Odyssey…
Grease
… before the fight plays out to You’re the One That I Want.
Gossip Girl
Deadpool says he has an extra bone when he’s watching Gossip Girl presumably because of all of the beautiful people in it, including Ryan Reynolds wife Blake Lively. Speaking of which, I am glad that they left the reveal that she was playing Lady Deadpool to the cast listing in the closing credits.
Loki
The first season of Loki is where we learn about the TVA, the Void and the smoke monster Alioth.
Van Wilder: Party Liaison
The Proposal
These are the two of Reynolds’ previous films mentioned when Deadpool and Nicepool both break the fourth wall before the latter is used as a human shield.
Thor
Any of the movies Thor is in will do to be honest. I wonder if we’ll ever find out why Thor was crying.
Avengers
The shawarma moment from the end of this film is referenced and the helicarrier is crashed in the Void.
Avengers: Endgame
This film is mentioned.
You also need to have a good appreciation of Chris Evan’s Captain America to understand his cameo…
Fantastic 4
… and to know that he first played Johnny Storm in 2005’s Fantastic 4.
Mad Max: Fury Road
Furiosa: A Mad Max Saga
Technically either of the last two Mad Max films will do although Furiosa is mentioned while the iconography of the Void vehicles mostly comes from the first one.
Doctor Strange in the Multiverse of Madness
The amateur wizard that Cassandra killed to get the sling ring could be Doctor Strange or Ned from Spider-Man No Way Home, but the statue of Wanda is from the second Doctor Strange film.
The Punisher (1989)
The Punisher (2004)
The Punisher: War Zone (2008)
The Punisher (2017)
Punisher is referenced as having been played by multiple people.
Man of Steel
Again, any of the appearances of Henry Cavill as Superman will be as good as any other for when you seen him as a variant of Wolverine.
The Incredible Hulk
Hulk is in the montage of alternate Wolverine’s as well.
Star Trek II: The Wrath of Khan
As Deadpool is on the other side of the glass facing certain death, he does the Vulcan salute just as Spock did when he was in the same predicament at the end of the second Star Trek movie.
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You also need to know about these Wolverine comics:

, as well Will Smith’s behaviour at the 2022 Oscars, and that Channing Tatum was trying to make a Gambit movie for years that never got off the ground.