Batman / Judge Dredd: Judgment on Gotham

In this landmark 1991 one-shot from DC Comics, writers Alan Grant and John Wagner orchestrated a brutal collision between two of comics' most uncompromising icons, with Simon Bisley delivering a fever-dream of hyper-detailed, grotesque art. The story pits Gotham's Dark Knight against Mega-City One's fascist lawman, forcing Batman to confront a Judge who answers only to the letter of the law rather than justice. This crossover stands as a definitive early meeting of the characters, setting the tone for their subsequent clashes with its stark, violent, and morally ambiguous premise.