Lex Luthor
Depending on the writer and how they handled the story, Lex could irrepentant or sympathetic. Lex used to be a fan of Superman until an accident happened that cost his hair and he blamed Superman for it. Lex doesn't want to kill Superman as much he wants to discredit him and make himself look good. I really liked his Smallville incarnation, he was actually cool and he was best friends with Clark but his fatal flaw combined with the events that occurred as the series progressed molded him into the villain he was destined to be. This incarnation of Lex struck a chord with me because Lex was a villain who didn't aspire to be but the circumstances in his life and his own failings is what led him to the dark side. It shows that while it is true that while man change their circumstances, the circumstances can change men.
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This is an awesome thread. To be honest, though, most villains qualify as failed villains simply because they inevitably lose to the protagonist at the end of the movie/series/book/etc.
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This can be said of most shonen, Disney movies, comedy movies or any media that has good and evil. It is pretty much a foregone conclusion that hero us gonna win against the villain but that doesn't necessarily mean that it is bad, it just an overused trope.
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Ambiguous villains do tend to be the best, in my opinion. But like you said, it's realism that's important.
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One of the most notorious is Ozymandias of Watchmen, you could root for him for averting a crisis or chide him for a ridiculous plan that may or may not had worked out.