Deadpool certainly rubs people up the wrong way. He's annoying, obnoxious, and has a penchant for violence that doesn't sit right with every hero. Nonetheless, he has made some pretty peculiar friends in the comics over the years that have certainly had fans scratching their heads.
Of course on screen, Deadpool has had a mixture of allies that seem ill-suited to one another. His partnership with X-Men like Colossus and Negasonic Teenage Warhead, as well as the formation of the X-Force, both demonstrate that he can form relationships in the strangest of ways. Needless to say, some of his friendships in the comics can get even more bizarre.
Honorable Mention: Wolverine
It would be a crime not to mention the alliance that has formed between the mutant Wolverine and Wade Wilson. Indeed, Logan hates partnering up with Deadpool and yet the duo has even shared a title together with both names getting top billing.
It really shouldn't work. Wolverine's lack of patience puts Deadpool in danger of having his head sliced off at every moment. Yet their shared trauma and violence in battle means they make useful allies when conflict arises. It's a strange partnership but one that fans are very familiar with now — even if Logan hates it when Deadpool tries to match their costumes.
Captain America
Captain America and Deadpool hold very different values, yet there's shared respect there, somehow. Deadpool looks up to everything Cap stands for, portraying the hero he could never be.
Steve Rogers has the great ability for empathy. He can understand Deadpool's own struggles and also acknowledges some of the mental health challenges he has overcome. They certainly have different methods but this chalk-and-cheese combination works. In many ways, it's a shame that Cap has bowed out of the MCU, considering fans may never see this duo on screen together.
Shiklah
Shiklah and Deadpool didn't just share a friendship but also a marriage. Their partnership was based around their shared love of murder. This odd couple worked because of this violence, although things crumbled when Wade tried to turn over a new leaf.
Shiklah would go on to marry Dracula instead, which caused a lot of conflict in regards to this jealous rivalry. When they were together, Shiklah only brought Wilson deeper into darkness, although his attempts at reconnection showcase how important that friendship is to him.
Agent-X
There have been some incredible MCU villains on-screen thus far, although it's difficult to tell if Agent-X will ever be brought in considering the complicated nature of his origins. The short version is that Agent-X has merged with Black Swan and Deadpool, considering them relatives in some way.
The character has been both an enemy and an ally to Deadpool but considering he's a sort of clone of Black Swan and Deadpool, their friendship is really quite strange. The unpredictability of the character means he should really be kept at arm's length.
Benjamin Franklin
Believe it or not, Deadpool and Benjamin Franklin are actually close friends. All sorts of strange events have taken place in the pages of the Deadpool comics, but one of the most bizarre was the resurrection of the founding father, albeit as a ghost.
Somehow the two characters just got on, although that may be in part due to the fact that Franklin hadn't really been able to talk to anyone living for a while and Wade is happy to have a conversation. Once again, Wilson's respect for the "American ideal" also comes into play here.
Constrictor
barely escaped development hell when it was being produced and that led to a lot of re-writes. It's difficult to know whether Constrictor was ever even considered to be part of the production, although he plays an important role in the comics.
The criminal actually lived with Deadpool for quite some time and could be considered to be one of the oldest friends to the Merc with a Mouth. It's strange that they get along at all, although Constrictor has worn just as many hats as Deadpool from his time with the Serpent Society to the Initiative and fighting on both sides of the law.
Deadpal
The Deadpool comics have a strange habit of bringing in alternate versions of the character. Whether it's Gwenpool or in this case, Deadpal, each one brings something different to the table. Having said that, none of the others have actually grown from Wade Wilson himself.
Deadpal was an alien Brood that grew from the inside of Deadpool. Although only featured in one issue, the two bonded, with this creature actually masking up in Deadpool attire and wielding duel weapons. It's the kind of odd partnership that Marvel really could only write for Deadpool.
Hydra Bob
Hydra Bob is one of Deadpool's most classic friends. The man that dons the iconic beast of Greek mythology on his gear somehow found a lot in common with the Merc with a Mouth. They often find themselves on different sides, although for Bo,b his gigs are more of a job than a total ideology.
Hydra Bob has become a beloved character for fans as a guy who's just trying to find his way through the henchmen community. Deadpool loves catching up with his old friend and will even allow him to get the upper hand from time to time if they do have to face one another.
A.I.M. Agent Bill
Hydra might have Bob, but A.I.M. (the organization currently well known for its role in Square Enix's Avengers game) enlists the help of the agent known as Bill. Much like Bob, Bill is simply a henchman who is trying to survive his day-to-day duties.
Deadpool considers himself a misfit and someone often overlooked so it's no surprise that he gravitates toward the henchmen community for friends. While Bill might not be as firm an ally as Bob has been, he has quickly become known for his work with Headpool (the severed head of Wilson).
Mercs For Money
Mercs for Money is a group that Deadpool helped to organize which might be composed of some of the oddest characters in Marvel history. It's a genuinely odd mixture of people and it's surprising that any friendships form from this money-driven partnership.
With the likes of Hit-Monkey, Gorilla-Man, and of course, Negasonic Teenage Warhead amongst the group, there are certainly some combustible elements at play. Regardless, there's a respect for Deadpool shared amongst the group built from their dangerous missions — yet also a distinct lack of obedience for his leadership.
