Despite being regularly regarded as something of a screw-up in the Marvel Universe, Deadpool has actually found some surprising friendships. While some make sense -- such as his surprising empathy with fellow Weapon X survivor Wolverine -- others, like his long-time association with Cable, can be more unexpected.
But perhaps one of the most surprising and humanizing friendships Deadpool has ever had was with a fellow mercenary, Taskmaster. So how exactly did Taskmaster and Deadpool go from heated rivals to unlikely friends?
Deadpool and Taskmaster first confronted each other in Deadpool #2 by Joe Kelly and Ed McGuinness. Taskmaster sought to use the nigh-unbeatable Merc with a Mouth as the ultimate show of skill to his pupils. But Deadpool's sheer unpredictability gives him the edge over Taskmaster, and Wade defeats him. Taskmaster vows to figure out how to beat him in the future, setting up their professional mercenary rivalry. He tried to kill Deadpool multiple times across their next handful of encounters, seeking revenge for his earlier defeat.
However, Deadpool would later find himself unexpectedly turning to Taskmaster for help. Earning the ire of the telepathic mercenary Black Swan, Deadpool found himself dealing with a mental virus. Trying to find the Black Swan, Deadpool ended up turning to Taskmaster at the request of his assistant Sandi, an ex-girlfriend of Taskmaster and friend. Over drinks, Taskmaster revealed what he knew about Black Swan, noting that he still wanted to kill Deadpool himself, but that'd be willing to help out if need be as a favor to Sandi. The two even attacked Sandi's current boyfriend when he beat her badly enough to land in the hospital, with Deadpool only sparing him thanks to a promise to Sandi (and one that Taskmaster conveniently never took).
Taskmaster and Sandi would later work with Agent X while under the assumption he was an amnesiac Deadpool, having survived his encounter with Black Swan. When the truth was revealed -- that Deadpool, Black Swan, and a mercenary named Nijo had effectively traded attributes in an explosion -- Taskmaster helped restore the two men and even was able to briefly reignite his relationship with Sandi. Deadpool called upon Taskmaster to help prove his skills in a fight, with Taskmaster outright admitting that he believes Deadpool is one of the skilled fighters he's ever dealt with, but also tries to share some advice to Wade about finally becoming professional.
Wade would continue to turn to Taskmaster for other missions, even helping Wade humiliate the Thunderbolts. Throughout it all, Taskmaster and Deadpool have developed a snarky relationship that goes back and forth between friendly, understanding, and cruel. Both men mock each other for their weaknesses, but they've become increasingly close over the years with both mercenaries even working with the other without any promise of pay, although they always try to take that. Taskmaster even has gone out of his way to help Deadpool survive his encounter with Norman Osborn. Taskmaster was even among the people Deadpool explicitly considered a friend (and ended up manipulated by Macho Gomez as a result), although Taskmaster would eventually betray him when his healing factor was removed.
When Deadpool tried to hire someone to finally kill him, Taskmaster was among the assassins who took a shot but it's revealed that it's far more for the challenge, as he (and Bullseye) refuse to help him merely end his life, and requests a throwdown when Deadpool is back to his normal self, telling his frenemy to get over himself.
With Taskmaster set to appear as the primary antagonist of the upcoming Black Widow and Deadpool now having the potential to appear in the MCU, the pair could have their unlikely friendship brought to the big screen. In fact, Taskmaster could end up being the perfect straight-man to Wade's ridiculousness, and be the connective tissue that binds Wade to the grander Marvel Universe.