Adventures Of Superman #445 1988

Adventures Of Superman #445, titled "Headhunter," finds Superman grappling with profound guilt after executing the Phantom Zone criminals, a pivotal moment leading to his eventual exile. Brainiac, inhabiting Milton Fine's body, desperately seeks human brains to stabilize his deteriorating form, resulting in the kidnapping of Cat Grant and Jimmy Olsen. This issue is notable to collectors as it marks the first appearance of the modern Brainiac and initiates a significant character arc for Superman concerning his moral compass.