Action Comics #123 (1948)

In Action Comics #123, you get to witness a group of 50 crime bosses try to find a way to take out Superman once and for all. The group ends up on a newly formed, volcanic island where they set up their base of operations. They hold a contest to see which method will work best to take out the Man of Steel. Superman, being Superman, overhears their plans but decides to help them out in their attempts. However, before doing so, he puts on a mysterious ring.

All of the physical attacks on Superman fail, but the bad guys come up with a new plan - to kidnap Lois and kill her, causing Superman to die of a broken heart. Lois is taken to the island, but of course, Superman saves her just in time. After that, he apprehends all the crooks on the island and carries the entire island back to the US, where he reveals that he has them all on film.

You'll definitely want to add this classic issue to your collection for its unique storyline and exciting plot twists.