While Spider-Man fought that first ‘Taskmaster’ long before the Avengers ever tangled with the official version of the villain.
Anthony Masters aka Taskmaster made his Marvel Comics debut in Avengers #195 by David Michelinie and George Perez. In the issue, the Avengers are looking into an institution for the criminally insane only to find out that it is a front for a villain training facility, and the expert fighter who is behind the villains’ training is none other than Taskmaster. Taskmaster was chosen to teach other bad guys how to fight like the heroes they hate because he has the ability to mimic the physical skills of anyone he observes. This makes Taskmaster an immense threat to anyone who challenges him.
In The Amazing Spider-Man #8 by Stan Lee and Steve Ditko, Peter Parker and his classmates are given a presentation by a renowned scientist and inventor who developed the greatest problem-solving machine ever built: the Living Brain. The Living Brain is a classic robot that can figure out anything given enough information, including someone’s fighting style. When the Living Brain goes off the rails, Peter Parker swings into action as Spider-Man in an effort to take it down. Unfortunately, that proved harder than anticipated as Spider-Man’s every move was perfectly copied by the Living Brain immediately after Spidey did them.
The Living Brain’s power set is eerily similar to those of Taskmaster, or rather, Taskmaster’s is similar to those of the Living Brain as the robo-villain made its first appearance nearly two decades before Taskmaster challenged the Avengers. However, while the Living Brain was around long before Taskmaster, Masters was a clear upgrade both in style and proficiency. The Living Brain has all but fallen into obscurity after Spider-Man eventually found a way to defeat it by the end of this issue, whereas Taskmaster has gone on to not only be a fairly constant thorn in the side of the Avengers, but also to lead his own ‘Suicide Squad-esque’ team of villains known as the Thunderbolts. Plus, Taskmaster’s aesthetic is undeniably awesome with the hooded skull face giving off an air of intimidation that is backed up by his nearly unbeatable skillset.
While the Living Brain was introduced before Taskmaster and wields the same impressive ability to replicate the physical skills of anyone it observes, Taskmaster overshadows the Living Brain greatly as a truly iconic villain. However, regardless of whose impact was longer-lasting, the fact remains that Spider-Man fought Marvel’s first ‘Taskmaster,’ and he did so long before the Avengers.