An old man with wings might not seem like someone worth worrying about, but Spider-Man has had some pretty epic battles with The Vulture over the years. Other younger men have borrowed the mantle, but Adrian Toomes is by far the most iconic version of this villain. He even unmasked Spider-Man at one point, but was horrified to learn that the man he had spent years facing off against was a complete nobody who he simply did not recognise. Had the movie not been scrapped, the plan was for John Malkovich to play The Vulture in Spider-Man 4. That would have been fun to see and is actually a perfect casting choice.