Here’s the story of how old Deadpool and Spider-Man once teamed up in their twilight years in comic form. Deadpool and Spider-Man are like The Odd Couple of the Marvel universe. The Merc with a Mouth is vulgar, morally questionable and tends to kill rather indiscriminately while Spidey – though he has his sassy moments – is more like a boy scout in comparison. Nevertheless, the unlikely duo complement each other when they get together and their pairings have become a fan favorite among Marvel’s readers.
Deadpool and Spider-Man have met up many times in the comics, like when Deadpool helped Spidey out by posing as the web-slinging wonder boy in Deadpool Annual #2 or when Deadpool flung Parker off a bridge in Cable/Deadpool #24. Their first official team-up, however, came with the Spider-Man/Deadpool series which recently published its fiftieth and final issue. During that series, Marvel readers saw the pair become good pals - or at least semi-functional frenemies - as they joined forces to battle various villains.
Spider-Man/Deadpool also introduced the three-issue Oldies arc which jumped way into the future and saw old man Deadpool and octogenarian Peter Parker living in the same retirement home. Whereas Deadpool is up to his usual tricks and having threesomes with his fellow nursing home residents - and sporting a wicked Santa-like bear - Spider-Man is in a wheelchair and seems to have lost his mojo in old age. That's until Deadpool convinces him to come out of retirement to take on an imposter who is posing as the Merc with a Mouth.
The intrepid but infirm duo bust out of their retirement home and track down the imposter who turns out to be a Life Model Decoy Deadpool created earlier in the series (and years ago, chronologically) when Deadpool and Spidey were captured by the Chameleon in Tabula Rasa. Clone Deadpool is about to trounce old man Deadpool when Spidey jams a device into the LMD’s leg which he thinks is a kill switch but actually summons an army of LMD Deadpools.
Marvel comics love jumping forward into the future to show readers older versions of Marvel heroes, with the best-known example being the Old Man Logan version of Wolverine that would inspire the 2017 film Logan. But whereas some older versions of Marvel heroes have rather grim futures, old man Deadpool and Spider-Man are more like the Golden Girls of the superhero world.