Deadpool Team Up Movies We'd Pay To See
Deadpool's wisecracks (and general insanity) are always fun, but even more so when he has somebody to bounce said wisecracks off of. Anyone who's read the wildly popular Deadpool/Cable comics can attest to that. And while his cinematic tag-team with Colossus will surely be memorable, there are plenty more people he could share screen time with during future sequels. Whether it's a fellow comedian or a rigid straight-person, one thing is guaranteed: they will want to punch Deadpool in the mouth. Okay, two things: the mouth punch thing, and that team-ups like the following would make for some awesome cinema.
Wolverine
After X-Men: Days Of Future Past, it only makes sense these two get a second chance together. As a duo, they're the best because they barely get along, if at all. Wolverine is gruff, serious, angry, and cracks jokes less often than a Greek tragedy. Deadpool, meanwhile, is none of those things, and genuinely enjoys trolling Wolverine until he explodes and initiates fighty time. A Wolverine/Deadpool movie would basically be an anti-buddy film, in that they'd begrudgingly co-exist the entire time, with their relationship inevitably ending once the two men embrace the only two things they have in common: hyper-violence, and an inability to die from getting hacked, slashed, and butchered to unrecognizability. It'd be like Batman vs. Superman, but with handshakes and supergroup-foundings replaced by decapitation and gaping stab wounds.
Spider-Man
A Spidey/Deadpool team-up almost has to happen, due to the two teaming up so much in the comics. But unlike Wolvie, Wade and Peter don't fight so much as they awkwardly get along. And by that, we mean Spider-Man awkwardly deals with Deadpool, who idolizes him in both a fellow-hero way, and in a bromantic and pseudo-sexual way. The feeling isn't mutual, especially in the latter department, but Parker's simply too nice a guy to kick the crap out of Deadpool and leave him lying in a pile of his own chimichangas. Plus, since both are red-suited amateur comedians, they're pretty much destined to do this forever. Put the two together in a film, emphasize the sexual tension as far as the MPAA will allow, flood the dialogue with jokes, and watch your audience hoot and clap with delight. If only 20th Century Fox (which holds the film rights to Deadpool and the rest of the X-Men) can make nice enough with Marvel and Sony (who share custody for Spider-Man's cinematic exploits) for this to actually happen.
Morph
Speaking of comedians: Morph might not have lasted long in the '90s X-Men cartoon, but he's since become a comic book fixture, so why not let him and Deadpool run amok? This is a case where there wouldn't really be a straight man, as both are unhinged and wacky enough to drive the other bonkers at any point. So in that sense, they might alternate between being the straight guy and the comic relief, until both completely ignore crime in favor of out-gagging one another.
Rogue
As attracted as he clearly is to her, Deadpool rarely interacts with Rogue in the comics. The reason why is both obvious, and interesting enough to drive an entire movie: Rogue might be one of the few people capable of outright killing the Merc. She can suck away somebody's life-force simply by touching them, remember, and not even the sweetest of sweet healing factors can heal you when you're literally a brainless, soulless husk. Even in the Deadpool video game, when he touches a fallen Rogue to save her life, he sacrifices just enough of himself to revive her, but not end him permanently. It's those kinds of stakes that a Rogue/Deadpool film would throw at him, and it would be real interesting to see how he deals with it. Especially since—let's be honest—he'd be super-tempted to touch Rogue even with the threat of actual death looming.
Iron Man
One of the more interesting aspects of Deadpool's personality is that he's usually broke, despite being a successful, highly paid mercenary. And unlike Spider-Man (the only other perpetually penniless superhero around), he has no interest in earning extra income legitimately. So why wouldn't he want to snuggle up to Tony Stark, the richest hero in the Marvel universe? Helping a billionaire philanthropist turn back Ultron, Loki, or whoever else might pester the Avengers would mean massive paydays for the mercenary—and if not that, at least enough free groceries to keep him drowning in pizza and pancakes until the world explodes. The two would probably get along well, actually: Iron Man's not as hilariously crazy as Deadpool, but he has quite the snarky sense of humor himself, and the two would likely find one another quite entertaining, as would the viewers. Once again, this'll only happen in our wildest dreams, since 20th Century Fox seems to have no intention of making a deal with Marvel to let the X-folks play in the cinematic Marvel Universe.
Magneto
Deadpool doesn't have to exclusively team with superheroes. Being the violent, rude, and amoral human being he is, if a villain like Magneto offers him enough money, why wouldn't he take that job? Against a group that includes people like Wolverine, Magneto would do very well to have his own near-immortal on his side, albeit on a contractual basis. That being said, their partnership would likely crumble by the second act, as Deadpool's constant pestering would quickly cause a miserable being like Magneto to violently snap and crush poor Wade under a giant pile of rubble. Once he recovers, Deadpool would seek revenge; not for any noble reason, but because Magneto stiffed him on pay. He just seems like the kind of guy to do that. Imagine Ryan Reynolds and Michael Fassbender splitting top billing on this thing...
Another Deadpool
Ultimately, Deadpool's best partner is himself, so why not make a movie with two hims? It could easily make storyline sense, too—these are comic book movies, after all, and cloning is absolutely a thing there. Whether Deadpool gets struck with a cloning ray, or locks himself in a cloning machine, or laces his favorite beer with cloning formula, there would soon be two Deadpools, each with the same twisted personality as the other. Would the Deadpools get along, or would the same sense of humor that causes everyone else to wish Lady Death would just take the Merc away already cause the two to turn on one another? More importantly, after the bad guys (and the good) are all dead, will the two Deadpools fall in love and get married? If he can't be with Rogue, after all, why not the next best thing? This also begs the question of who would wear the dress. Probably both of them.