2) Ben Affleck – Daredevil
Ben Affleck was suffering from a lot of scrutiny during the early 2000s. His relationship with pop singer and actress Jennifer Lopez was getting covered by the media 24/7, and he was starring in a string of critical and commercial flops, including Paycheck and Gigli.
But the one film that would end up haunting him the most was Daredevil. Affleck portrayed blind lawyer Matt Murdock who becomes the titular anti-hero in order to ensure justice is delivered to everyone who escapes the criminal justice system. While Affleck’s performance itself was fine (alongside the rest of the cast, including the underrated Michael Clarke Duncan as Wilson Fisk/Kingpin), the other parts of the movie ended up bringing it down, from the script which featured horrible scenes like the seesaw fight, to the editing which changed the film from an R to a lighter PG-13 (something that would be fixed in the Director’s Cut).
As such, the pic ended up receiving mixed reviews, and Affleck swore off comic book movies altogether. Of course, that all changed when he decided to take on the role of Bruce Wayne/Batman in Batman V Superman: Dawn of Justice. But considering that Daredevil was his favorite superhero growing up, Affleck’s inability to be a part of a successful series with the property, as well as the derision it left on him in the months leading up to Dawn of Justice’s release, makes it is no surprise why he regrets it the most.