Wolverine
Wolverine’s future is totally up in the air at the moment, with Fox not immediately considering recasting the X-Men leader after Hugh Jackman bowed out of the role with this year’s Logan. It’s vaguely possible, then, that Marvel could acquire the rights to the character at some point. And if that did ever happen, the first port of call would be to have him team up with Spider-Man.
Unlike Spidey and Deadpool, the joy of a partnership between Peter Parker and Logan is their completely opposing personalities. Wolverine is a cynical old soul who’s seen it all while Peter is a peppy, wide-eyed kid. That said, the pair can go toe-to-toe in a fight and the question of who would beat who in a brawl is one fans would love to see answered on screen.
The tragic thing is, we could have had this crossover already. Back in 2002’s Spider-Man, Hugh Jackman was offered a quick cameo in the movie but the whole thing fell through due to, of all things, a hiccup with his costume. But hey, Jackman has said he would consider playing Wolvie again in the MCU. So maybe this could take place for real one day…