While I very much agree with Andrew Ryan and GLaDOS as rating among the best ever game bosses, I want to throw out some ones that might not get as much appreciation and are a little less obvious.
Oh, and by the way, SPOILERS.
Teyrn Loghain from Dragon Age: Origins - Loghain strikes me as one of the most interesting and unappreciated villains in all of video games. It's so easy to fall into the stereotypical big baddie archetype without providing them with any more richness of character. Loghain makes two very significant transformations during the game's story arch - the first occurs right at the start of the game, where the man considered a national hero and the most loyal of men betrays his own king and almost dooms his country, at which point he assumes power. Loghain works as a character to me because he is not a simple case of being evil; he is a man who acts based on prejudices that have been engrained in him through his life, rather than wilfully acting evil to screw people over. The game's penultimate act at the Landsmeet in Denerim, where Loghain's plans come crumbling around him, reveals his true character in a brilliant way. He was willing to do absolutely anything he could to protect his land, but he was misguided, blinded by rage, and he completely failed to realise that the Darkspawn posed a much greater threat than the Orlesian enemy he so passionately despised. Loghain is a tragic figure, a soldier through and through, who knows only the cruelty and hatred of war. He's also loyal to the last, but is entirely unfit to lead a nation. He took over power in Ferelden because he believed that nobody else would have the courage and the foresight to save the land. He was wrong, but his intentions were almost admirable. This is the kind of depth and complexity that defines truly excellent character creation; it's something that BioWare has made a reputation on, and Loghain is one of their best.
Dr. Wallace Breen from Half-Life 2 - the silent protagonist is a difficult role to pull off, but it is possible if you surround your speechless hero with fully realised and nuanced characters. Such is the case of Gordon Freeman, who has become an icon among gamers without saying a single word, but some of his supporting cast have become just as famous and celebrated, from the chirpy and slightly meek Dr. Kleiner to the straight-talking beer-owing soldier Barney to the loyal girl-next-door comrade Alyx Vance. But for me, Half-Life 2's best character is Dr. Breen, the malevolent puppet leader of the oppressing force, the human simulacrum of the Combine. Again, Dr. Breen is not simply evil, but he has a very clear view of humanity's future. He seems like the only character in the universe who has accepted humanity's doom as a reality, and thus wishes to make the best of a situation that is all kinds of fucked up, and that he, as the administrator of the Black Mesa Research Facility, played a part in causing. Some of Dr. Breen's dialogue is absolutely brilliant, and although you don't actually see the character in person until the very end of the game (except for a very brief moment during the first chapter where you are teleported momentarily to his office), you are constantly reminded of his presence by the large screens scattered around City 17 which broadcast his dystopian message. Dr. Breen has to carry an awful lot of the weight in telling Half-Life 2's subtle but entirely wonderful story, and although the final pay-off for the character comes with an entirely disappointing boss battle, he is without doubt one of the most memorable and affecting characters in recent memory.
Kurt Dierker from The Saboteur - Developer Pandemic Studios' swan song was regarded as a pulpy, stylish and somewhat engaging open-world adventure, but suffered from gameplay issues and some rough edges, as well as, and I quote Ryan Davis, "a sense that its best tricks are borrowed from other, better games." My appreciation for The Saboteur is greater than most, and one aspect of the game that I felt Pandemic got so little credit for was creating a Nazi who didn't feel like the archetypal big bad fascist. This sense is mostly due to two particularly effective sequences during the game. The first takes place during the game's opening chapter, which shows mechanic turned race driver Sean Devlin taking on Dierker at the Saarbrucken Grand Prix race, mere months before the Nazi invasion of France. Devlin believes Dierker to be a simple cheating asshole after Dierker shoots out Devlin's tyres in order to win the race, but soon afterward they realise that Dierker is much more than he seems. He is actually a high ranking Nazi officer who ends up killing Sean's best friend in cold blood, beginning Devlin's revenge tale. At this point he becomes the ever present malevolent force hanging over the resistance in Nazi occupied Paris, but his second key moment, the game's brilliant ending scene atop the Eiffel Tower, presents Dierker as a vulnerable and desperate man, scared of his fate, and possibly even remorseful over all the violent acts he has committed in the name of the Fuhrer and his Reich, the perfect depiction of the fragile insanity that defined Hitler's regime. It also becomes incredibly apparent how similar the two men are, as they fought so devotedly for their individual causes, crossing the blurred line of morality on several occasions and doing whatever needs to be done. Dierker's last line is "He are going to Hell, aren't we, Irishman?". It's an amazingly powerful moment, and one that should not be forgotten. Even if you don't want to play the game, find a video online that shows you the key moments in The Saboteur's story. You won't regret it.
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