Serving as an ambitious crossover of seemingly almost all major pieces of fiction, The League of Extraordinary Gentlemen was able to recontextualize some iconic figures in exciting ways. This meant reimagining chosen heroes like Harry Potter into pitiful monsters or exploring the complex motivations of someone like Captain Nemo.

But one of the grimmest such explorations came with one of the film's most famous espionage characters. Jimmy Bond from The League of Extraordinary Gentlemen was one of the darkest versions of James Bond that's ever been introduced -- remaining the suave super-spy as a major antagonist and enemy of the titular team.

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The League of Extraordinary Gentlemen was a way for co-creators Alan Moore and Kevin O'Neill to explore the history of literature and cast a modern lense over some of the most iconic figures in fiction. Although the early storylines focused heavily on Victorian-era creations, the Century trilogy highlighted figures from across the 20th and early 21st century -- including one of the grimmest renditions of James Bond ever conceived of. The grandson of Campion Bond -- who has been the League's handler during the first two volumes of the series -- Jimmy was formally an agent of MI-6 who came up against Mina and Quatermain during their attempts to procure the Black Dossier.

A thuggish and brutal agent, Jimmy Bond lacked any of the grace or humanity of most of his counterparts. Instead, Jimmy was a more bluntly dark version of the character. He didn't even ultimately have any real loyalty to England, as it was revealed he'd quietly become a double-agent for the United States as well. Instead of being a rogue romantic who could seduce any woman he met, Bond is portrayed as a violent brute, whose attempts to force Mina to have sex with him quickly turn violent. Notably, Bond's crimes largely pay off -- with the villainous take on the super-spy covering up his actions and arranging for his elevation within MI-6 in terms of power and respect. It's a take on the spy character who genuinely can't be controlled -- and highlights why that'd be so scary.

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However, it was time that would prove his ultimate enemy. As he aged, the consequences of his earlier escapades caogut up to him, leaving the eventually decrypt old man suffering from a number of diseases and physical ailments that left him in constant agony. League of Extraordinary Gentlemen: The Tempest concluded the series by positioning Jimmy as one of the final ultimate antagonists -- especially after he used the Fountain of Youth to restore himself while he targeted the mysterious Blazing World. But his attempts to bring down the heroes ultimately resulted in the collapse of MI-6, the eradication of most of his allies, and his eventual death at the hands of Emma Night, a former romantic conquest who'd long ago learned about his truly duplicitous side.

Jimmy Bond is one of the darkest portrayals of the famous super-sup in any form of fiction, reimagining one of the genre's most enduring characters as a monster. It takes all of the elements of the character that haven't aged well, and focuses the spotlight onto them. It's notable that Jimmy Bond isn't even a mastermind or existential threat like many of the other dangerous foes of the series. Instead, Jimmy is a representation of the vicious side of adventure heroes, every bad impulse and lack of consequence molded into a single subversive take on Britain's most famous spy -- and one that provides a perfectly designed contrast to the inventive and heroic women who'd taken the lead of the series by the events of The Tempest.

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