Gah!
Can there exist such a person as to reject the awesomeness that is Holland Manners? 😀
It's hard to explain, and my affection for the character owes much to the utterly chilling performance by Sam Anderson. I will do my best to explain why I feel Holland is so awesome.
Consider Mayor Wilkins. For fandom, the Mayor is one of the more popular Buffyverse villains; indeed, he's one of my very favorites, too. Where Wilkins loses points with me is that he's too likeable; very few are the moments where he exudes any sort of frightening behavior. Even his line to Buffy in the Library about "eating her" (the innuendo is thick!) came off somewhat lackluster. Wilkins is no Magneto; he isn't a villain with a sympathetic cause, so his likeability should be minimal.
Holland and the Mayor have similar dispositions. They both hide their nature behind a fatherly affection. Where the Mayor fails and Holland succeeds in my opinion is that you can tell Holland's is just a big lie. A tremendous hoax. There is a deep, sadistic arrogance to the man. His manners (pardon the pun) are laced with condescension, which screams "You're retarded if you think I honestly care about you," unlike the Mayor's genuine affection for faith. Not to mention Holland uses words like "crap" and references his "crazy youth." He seems less like an uppity, if affectionate, father figure and more like a dad who might let his underage son have a beer.
Holland is a conniver and a liar, playing God, resurrecting Darla, letting her wallow in her failing mortal coil for months, before arranging her "execution." Then he has the audacity to, in that psuedosympathetic guise, deliver her the news that she's going to succumb to the same illness that nearly killed her before. He ruthlessly manipulates his protege and condescendingly mocks him for his feelings for Darla.
To me, his stand out performances were "Blind Date" and "Reprise." In "Blind Date," the mindgames he plays with Lindsey are unbelievably sinister. He toys with both him and Lee Mercer and, before having Lee shot, toys with him by offering false apologies.
Holland, knowing that Lindsey betrays him, lets him go (after scaring the bejeezus out of him, of course) in a complex gambit: he knows, ultimately, that Lindsey will return. That his ambition is too powerful. He's an incredibly astute judge of character. He lets Lindsey sabotage an important project; lose the battle, win the war.
The parallels between Holland and Angelus are also considerable. While Holland is similar to Wilkins in his public personality, his mind is very much like Angelus's. To me, he represents Angelus if the vampire were truly a company man.
I could go on and on. Suffice it to say that the man was utterly chilling; second only to Angelus. He represented the pinnacle of Wolfram & Hart's philosophy, and it's testament to the man that we were treated to many references to his "brilliant mind" even long after his death.