Appearing in "The Legend of Greenbeard Olsen"
Synopsis for "The Legend of Greenbeard Olsen"
When genealogist Peter Shaw of the Genealogist society stops by the Daily Planet, he shows Jimmy the Olsen family tree and Jimmy learns that he is the descendant of Greenbeard Olsen, a buccaneer from the 1700's. He tells Jimmy that every generation a male descendant of Greenbeard would revert to a similar personality under a full moon. Shaw, wishing to disprove this superstition, asks Jimmy to accompany him on a specially reconstructed pirate ship. Perry White, thinking it would make a great story for the Daily Planet sends Jimmy, Lois Lane and Clark Kent to cover the story. Before going, Jimmy is asked to sign a contract making him liable for any damages done should he "turn pirate."
As it turns out, Jimmy apparently does become "Greenbeard" in personality whenever he puts on his costume, and becomes more and more tyrannical. Making Clark walk the plank (although he is pulled out shortly after a quick brush with sharks) and later locked beneath the ship. With each lapse into his Greenbard persona, Jimmy would eventually return to normal with no recollection of what he had done. Locked up in the hold, Clark is able to go into action secretly as Superman and prevent "Greenbeard" from destroying passing ships with cannon balls.
Eventually, the ship crashes into an iceberg, and despite Superman's secret aid, it still sinks putting Jimmy in the hock for $25,000 for damages done to the ship. Returning to Metropolis, Jimmy soon learns that his ancestor Greenbeard was really a double agent that hunted pirates, and that he had inherited Greenbeard's gold due to the fact that he was the first direct male descendant of Greenbeard. When Shaw tries to collect it for damages when Superman enters the room with a man bearing a striking resemblance to Jimmy. Superman reveals that Shaw orchestrated the whole ordeal in order to swindle Jimmy out of his inheritance and had an impostor pose as Jimmy whenever he was "Greenbeard" and carts Shaw and his men off to prison.
Appearing in "Wonder Lad"
Synopsis for "Wonder Lad"
With things quieting down in Metropolois, Superman decides to go on his monthly patrol around the Earth doing super-deeds. This in turn causes crime in Metropolis to skyrocket. Deciding to do something about it, Jimmy Olsen dawns a durable suit that Superman brought to him from another world and decides to fight crime in Metropolis as "Wonder Lad."
Jimmy becomes a news sensation, and the idol of a young paper boy named Tommy, who Jimmy mentors, giving him souvenirs of his exploits and giving him a signal pen to call Wonder Lad if the boy spots any trouble. When crooks take note that Tommy has a relationship with Wonder Lad, they kidnap the boy to try and learn what Wonder Lad's secret identity is. When Tommy calls for help, Wonder Lad arrives, but shockingly his indestructible suit shatters to bits, and Jimmy is unmasked and taken hostage with Tommy.
Without Jimmy's Superman signal watch, Tommy tries his signal pen to contact Superman, using a nearby radio broadcasting tower to boost the signal. The gambit works and Superman soon comes to their rescue. Later, Jimmy gives Tommy the Wonder Lad helmet, since without the indestructible suit his career as Wonder Lad is over.
Appearing in "The Wedding of Jimmy Olsen"
Synopsis for "The Wedding of Jimmy Olsen"
When Perry White assigns Lois Lane to write a story about how great Jimmy Olsen is, Jimmy misinterprets her assignment with the idea that Lois is falling in love with him. Not wanting to "steal" his best pal's girlfriend, Jimmy tries his best to appear to be a cad to Lois, however each time his schemes backfire and Lois continues to believe that Jimmy is a noble person.
Eventually, Jimmy gives up and proposes to Lois, when Lois tells Jimmy that she is in love with the sweetest man in the world, Jimmy still believes it is he that she is talking about, instead of Superman. The concept of being married frightens Jimmy who imagines what it would be like marrying Lois and raising a family.
After telling Superman of the mix-up, Lois and the Man of Steel come up with a way to cancel their engagement. Pretending to be out to purchase a ring with Jimmy, Lois feigns being upset when Superman comes to get Jimmy for a story. Lois then pretends to be insulted being considered second fiddle to Superman and cancels their engagement. Jimmy is relieved that she did so, and is off the hook. Later, after the story is published in the paper, Jimmy boasts that he hopes that it doesn't cause other women to fall for him and his "manly charms."
- The man from the Maritime Bank tells Jimmy that he inherited Greenbeards gold because he was the first direct male descendant of Greenbeard. However, Peter Shaw's genealogy chart shows at least two other male descendants of Greenbear that predate Jimmy: Eric Olsen, and Lars Olsen. It's possible that Shaw's chart was purposely inaccurate.
- This issue is reprinted in its entirety in Showcase Presents: Superman Family #1.
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