Character Analysis
Can a villain get any more villainous? Count Olaf has to be one of the most dreadful and thoroughly terrible bad guys ever to grace the pages of a novel. He'd even give Iago, Simon Legree, or the White Witch a run for their money.
Bad to the Bone
From the first moment that the Baudelaires meet Count Olaf, he's clearly bad news:
"Hello hello hello," Count Olaf said in a wheezy whisper. He was very tall and very thin, dressed in a gray suit that had many dark stains on it. His face was unshaven, and rather than two eyebrows, like most human beings have, he had just one long one. His eyes were very, very shiny, which made him look both hungry and angry. (2.39)
Oh, man—not only does Count Olaf look bad, his house is in a shambles and he's got this weird tattoo of an eye on his ankle. No, this isn't just a bad first impression. The Baudelaires figure out that Count Olaf is exactly as terrible as he seems. He "was neither interesting nor kind; he was demanding, short-tempered, and bad-smelling. The only good thing to be said for Count Olaf is that he wasn't around very often" (3.3). Wow. This guy is about as awful as they come.
Not So Fortunate
The Baudelaires find out pretty quickly that Count Olaf has only one reason for adopting them: He wants to get his hands on the enormous fortune their parents have left behind. He has so little interest in the children otherwise that he doesn't even give them their own bedrooms. Or more than one bed. Or a dresser for their clothes. They have to stack everything in an old refrigerator box. Seriously.
Count Olaf becomes violently enraged whenever he doesn't get what he wants. He almost injures Sunny when the children don't have roast beef for him, he smacks Klaus for complaining about the lack of beds in their room, and, of course, he imprisons Sunny in order to force Violet to marry him so she can steal their fortune. Not one to be deterred by his own horrible behavior, Count Olaf gloats about how much smarter he is than three children:
"I may be a terrible man," Count Olaf said, "but I have been able to concoct a foolproof way of getting your fortune, which is more than you've been able to do." With that, he began to stride toward the house. "Remember that, orphans," he said. "You may have read more books than I have, but it didn't help you gain the upper hand in this situation." (9.22)
Thing is, Count Olaf isn't as clever as he seems at times. While it's obvious that he does have some kind of ulterior motives for getting the children to be in The Marvelous Marriage, he probably doesn't have the whole plan worked out—instead, it's Klaus who gives him the details. Really. So even though Count Olaf clearly believes he's much more clever than the Baudelaires, we think he actually needs their help a little when it comes to masterminding.
Acting
Count Olaf makes his living as an actor, which sort of fits with his evil personality—he travels around pretending not to be a villain for the benefit of people like Mr. Poe or Justice Strauss. He's also extremely vain and he clearly loves preening about on stage:
It will be of no interest to you if I describe the action of this insipid—the word "insipid" here means "dull and foolish"— play by Al Funcoot, because it was a dreadful play and of no real importance to our story […] Count Olaf had a great number of very long speeches, which he performed with elaborate gestures and facial expressions. No one seemed to notice that he held a walkie-talkie the entire time. (12.34)
Count Olaf might put on a suitable act for other adults, but the Baudelaires see him for what he is: a dreadful and wicked man. And it seems he might also be a playwright with diabolical intention—as you may have noticed, the letters in the name "Al Funcoot" can be rearranged to form "Count Olaf." Could he be behind the insipid play that everyone is forced to sit though? He's done so many terrible things that adding bad theater to his list of crimes doesn't seem like too much of a stretch.
Count Olaf's Timeline