Count Olaf

Olaf takes the Baudelaires into his run-down house, puts the kids to work for his troupe and barely hides that he wants the inheritance. In the show, he even welcomes the orphans with a musical number alongside his actors. Since the fortune only becomes available when Violet turns 18, he sets up The Marvelous Marriage, a play in which he would marry her for real.

The plan fails because of Violet's signature, and Olaf escapes, swearing he'll be back.

From then on, Olaf turns up with every new guardian in a disguise. As Stephano, Uncle Monty's assistant, he kills the herpetologist. As peg-legged Captain Sham, he leaves Aunt Josephine to the leeches. As the receptionist Shirley, he teams up with Dr. Orwell at the lumber mill.

Every time he's unmasked, the ankle tattoo gives him away, and he escapes.

At Prufrock, Olaf becomes Coach Genghis and kidnaps the Quagmire twins. He gains an ally and girlfriend, Esmé Squalor, and changes faces again: the auctioneer Gunther, Detective Dupin, Dr. Mattathias. As Gunther, he tries to smuggle the Quagmires out of the city inside an auction lot.

In the village of crows, he gets the Baudelaires accused of murder. At Caligari Carnival, he burns everything down and keeps Sunny.

In the Mortmain Mountains, Olaf reunites with his old mentors, the Man with a Beard but No Hair and the Woman with Hair but No Beard. Aboard the submarine Carmelita, he locks up the Baudelaires and gets his hands on the deadly fungus from the grotto. Then he chases the sugar bowl to the Hotel Denouement, where he forces the orphans to hold the harpoon gun that kills Dewey, and escapes in the same boat as them.

On the final island, locked in a cage, he's struck by Ishmael and infected by the fungus. Before he dies, he carries Kit Snicket, his former fiancée, to the beach.

In the 2004 movie, Olaf is played by Jim Carrey, in a much more comic tone than the books. He shows up as Stephano and as Captain Sham before attempting the wedding with Violet. Klaus burns the certificate, and Olaf is arrested and sentenced to suffer the same misfortunes he inflicted on the orphans, but he vanishes.

Neil Patrick Harris plays Olaf in the Netflix series and sings the opening theme, "Look Away." In the 2004 movie, the role goes to Jim Carrey, who shaved his head to make the makeup easier.