Deadpool and Spider-Man have a long history together. They have very similar personalities and team-up quite often in the cartoons and comics, to say that their BFFs would be an understatement. Sadly, we'll probably never see the two team-up on the big screen due to the fact that Sony and Marvel have Spider-Man under their ownership and Deadpool is owned by Fox so they legally can't cross-over unless Fox comes to an agreement with Marvel (but that'll probably never happen).
However, Deadpool 2 director David Leitch said that the teaser that appeared ahead of Logan back in March may hold a secret, probably unofficial connection to Spider-Man. For those who haven't seen the teaser or don't remember, Wade Willson sees an old man getting mugged and he then runs into a phone booth to slowly change into his Deadpool costume. He takes way too long to actually don the suit and the old man gets gunned down. Deadpool then goes and lays down next to the man's body and chows down on a container of Ben and Jerry's ice cream.
Of course, Spider-Man's origin story revolves around one major event: the death of the only father figure in his life, Uncle Ben. The character put the weight of the death of his uncle on his shoulder and took responsibility. Peter Parker had the chance to stop a robber but didn't and the robber killed Ben shortly after, it was a coincidence but it helped shape the character of Spider-Man.
For months people have been wondering if that man in the Deadpool 2 teaser is indeed Uncle Ben. After all, we haven't seen Uncle Ben in the MCU but we know he is dead as it's referenced in Spider-Man: Homecoming and Captain America: Civil War.
Speaking to Huffington Post, Leitch was asked about the possible connection and teased that the old man is certainly someone of note.
“That’s a really interesting question,” said Leitch, coyly. “I think that people should continue to theorize who that old man was.”
He didn't confirm if it was Uncle Ben but he also didn't outright deny it.
Deadpool 2 is set to release on June 1st, 2018.