The Punisher #56

Part four of the seven-part "The Final Days" arc, this 1991 Marvel issue drops us straight into "Prison!" — and the cover by Joe Quesada and Jimmy Palmiotti makes the stakes viscerally clear. A figure tagged "Castle" staggers forward in tattered bandages, clothes torn and scorched with glowing cracks, escaping what appears to be a grim island fortress rising behind him — all under the looming shadow of the Punisher's skull. It's a striking, unsettling image that promises a Frank Castle pushed well past his limits.