<Li> Sara Rue as Olivia Caliban, a librarian at Prufrock Preparatory School who later enlists as a member of the Baudelaire family's secret society when she becomes invested in the Baudelaires' plight . </Li> <Li> Nathan Fillion as Jacques Snicket, the dashing adventurer brother of Lemony Snicket who enlists Olivia Caliban to help the Baudelaires . </Li> <Ul> <Li> Joan Cusack as Justice Strauss, a judge and Count Olaf's neighbor who helps the Baudelaires and is hopeful to adopt them . </Li> <Li> Luke Camilleri as Gustav Sebald, a member of the Baudelaire family's secret society and Monty's former assistant . </Li> <Li> Aasif Mandvi as Montgomery "Uncle Monty" Montgomery, a distant relative of the Baudelaires and enthusiastic herpetologist who claims to have spent his childhood with their late parents . He is a member of the Baudelaire family's secret society and possesses a spyglass . </Li> <Li> Alfre Woodard as Aunt Josephine Anwhistle, a distant relative of the Baudelaires at Lake Lachrymose who has many rational and irrational fears and a love of grammar . She is a member of the Baudelaire family's secret society . </Li> <Li> Don Johnson as Sir, the cigar - smoking owner of Lucky Smells Lumbermill . </Li> <Li> Catherine O'Hara as Georgina Orwell, an optometrist and Count Olaf's ex-girlfriend who hypnotizes the Lucky Smells Lumbermill workers so they never leave, also causing them to believe the Baudelaire parents set fire to Paltryville . O'Hara previously portrayed Justice Strauss in the 2004 film adaptation . </Li> <Li> Rhys Darby as Charles, Sir's partner . </Li> <Li> Timothy Webber as Jimmy, a worker at Lucky Smells Lumbermill . </Li> <Li> Chris Gauthier as Phil, an optimistic worker who befriends the Baudelaires during their stay at the Lucky Smells Lumbermill . </Li> <Li> Loretta Walsh as Norma Rae, a worker at Lucky Smells Lumbermill . </Li> <Li> Trent Redekop as Cesar, a worker at Lucky Smells Lumbermill . </Li> </Ul> <Li> Joan Cusack as Justice Strauss, a judge and Count Olaf's neighbor who helps the Baudelaires and is hopeful to adopt them . </Li>

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