The two men born Winslow Schott on Earths One and Two were prolific inventors, incorporating advanced mechanical and theorectical principals into their designs of his state-of-the-art toys. The Earth-One Winslow and ewas a lad with long brown hair, traumatized at a young age when his neighborhood friend stole to first toy he ever assembled, a toy plane, which led him into a life of crime. The Earth-Two Winslow simply was an adult with curly blonde hair who simply decided to pursue a life of crime to quell his insatiable greed. Both men pursued similar paths towards infamy, each renaming himself Toyman, devising various schemes with various childrens playthings incorporating deadly devices. Yet time and time again, the Toymen were opposed and ultimately defeated by the Supermen of their respective worlds. Even when each allied the Luthor and Prankster of his Earth, both Toymen found only further failure.
At a certain point on Earth-One, Winslow grew older, now with whiten hair, and decided to retire as he set up a toy shop of his own. During this period of time, a younger usurper to his title stole the Toymen identity, and began plunder Metropolis with more advanced weaponry than his predecessor. This Toyman, Jack Nimble, incurred the attention of both Superman and Schott-One, who teamed up to capture this copy-cat crook. Nimble would reappear twice more, working on his own employing a separate sinister scheme, and later allied with fellow foes of Superman led by the alien Mr. Xavier.
Meanwhile on Earth-Two, Winslow retired for decades before returning to terrorize Metropolis once more. This time, Toyman was opposed both by Superman, and his old adversary's Kryptonian cousin Power Girl. Given Schott’s appearance, this encounter took place in the mid-1970s. When an older grizzled Schott returned years later, he faced a different Dynamic Duo defending Metropolis, Robin and Huntress!
The original Toyman of Earth-One was motivated to resume his criminal career once more, when his prized display at a toy exhibition was destroyed by an individual appearing to look like Superman. In fact, this was the Man of Steel's imperfect duplicate Bizarro, who returned to Earth-One in a crazed mental state. Reverting to his negative impulses, Schott sought out the two men he felt destroyed his life, Nimble and Superman! Schott slayed Nimble while the younger Toyman laid sleeping in his apartment. However, Superman was harder to kill, and turned the tides on Schott when it was revealed that Bizarro was the true culprit behind the destruction of Winslow's collection.
Contemporaries of each Winslow Schott were the Pranksters of each Earth, each born as Oswald Loomis. These two Pranksters had remarkably similar careers, with each at times teaming up with the Toymen, the Luthors, and the 5th Dimensional pests who plagued the Superman (Mr. Mxyzptlk on Earth-One and Mr. Mxyztplk on Earth-Two). As for the Earth-Two counterpart to Jack Nimble’s Toyman, this was a crook named Al Fresco, former protégé turned rival of Schott's fellow fiend the Prankster who adopted the alter ego of the Trickster*. Fresco wore a disguise at times making himself appear to look like the Prankster, and used similar gadgetry used by his insidious inspiration and the Toyman.
* Evidence suggests that on a few occasions after his introduction, Trickster disguised as Prankster who clashed with the Earth-Two Superman, given the frequently of a "Prankster's" appearances in the late 1940s and early 1950s.
