From the moment Lena Luthor was introduced in the second season of The CW's Supergirl, it felt like only a matter of time before her diabolical half-brother, Lex, would appear. Sure enough, the super-villain finally stepped out of the shadows about half-way through Season 4, with his megalomania and hatred of all things Kryptonian intact. But as infamous as Lex is for his obsession with Superman, he ironically ended up becoming Kara Danvers' greatest enemy.

While there was a lot of excitement surrounding Lex's debut on Supergirl, many people were taken aback when Jon Cryer was cast in the role. The actor already had a connection to the villain, having played his nephew Lenny in Superman IV: The Quest for Peace, yet he was better known for his portrayal of the hapless Alan Harper on Two and a Half Men, among other comedic characters. Even Cryer admitted he thought he was an odd choice when the show's creatives first approached him.

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If anything, casting Cryer against type proved to be the perfect move. His version of Luthor is brilliant and narcissistic, yet Cryer imbues him with a sense of charisma and dark wit that's essential to making the character work. Case in point: his first appearance on Supergirl, in the episode "Oh Brother, Where Art Thou?," culminates with a scene in which Lex calmly evades capture by the authorities by setting off hidden high-tech security traps around his mansion -- while pretending to conduct a symphony performance of "Eine kleine Nachtmusik." If that's not Lex Luthor in a nutshell, nothing is.

Building on that, Supergirl went on to reveal Lex was the real puppet master pulling the strings of the characters' who'd previously appeared to be Season 4's primary antagonists: Ben Lockwood, the Children of Liberty and Kara's double, aka Red Daughter. It turned out Lex's schemes went even deeper than that, with subsequent episodes revealing he had been plotting against Kara and Lena for years from behind bars in Stryker's Island Penitentiary. Even Lex's mother Lillian, a brilliant criminal mastermind in her own right, never came up with such an elaborate scheme when she served as the main villain in Season 2.

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Melissa Benoist and Jon Cryer in Supergirl Season 4

While he may lack the super-human abilities of Supergirl baddies like Reign and Gamemnae, Lex makes up the difference by always staying one step ahead of everyone else. At the same time, he's far from omnipotent and capable of making mistakes, like underestimating Lena before she shoots and kills him at the end of Season 4. Of course, he still got the last laugh by revealing Kara's secret identity to his sister before he died, setting the stage for Lena to become a quasi-villain in Season 5. It seems not even death can stop Mr. Luthor from wreaking havoc on the world.

Fortunately, that wasn't the end of his story. Almost immediately after his death, Lex was resurrected by Mar Novu, who revealed he had an important role to play in the impending "Crisis on Infinite Earths" brought about by Novu's destructive counterpart, Mobius. Sure enough, Lex ended up fighting alongside the other Paragons of the Arrowverse in the final battle against Mobius, before helping to create a new multiverse to replace the one Mobius has destroyed.

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Of course, part of what makes Lex a terrific villain is he never does anything for the greater good unless he can find a way to serve his own purposes along the way. And sure enough, Lex changes things so that, in the post-Crisis version of Earth, he's actually a well-respected philanthropist who controls the D.E.O., which makes him Kara's boss. And while he would go on to do some good in this new reality by helping Kara and her allies take down the sinister organization Leviathan, he also forced Brainiac-5 to betray his friends and serve as his double agent, before revealing he'd used Brainy as part of an even bigger plan to -- you guessed it -- kill Kara once and for all. It might be a new multiverse, but it's the same old Lex.

Jon Cryer and Jesse Rath in Supergirl Season 5

Due to the COVID-19 pandemic, Supergirl Season 5 was unable to complete production earlier this year, so Lex's latest scheme won't be resolved until the show's sixth and final season is released in 2021. Still, whatever happens in the show's remaining episodes, the odds are against Season 6 featuring a new villain who's anywhere near as darkly funny, yet persistently dangerous, as Lex has proven to be.

Returning to The CW in mid-2021 for its final season, Supergirl stars Melissa Benoist as Kara Danvers, David Harewood as Martian Manhunter, Chyler Leigh as Alex Danvers, Nicole Maines as Dreamer, Jesse Rath as Brainiac-5 and more.

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