Ethan Canin, author of "The Palace Thief" (upon which the movie is based) appears as one of the Board members around the table during Hundert's meeting with the school's board of directors. He is seated on the Headmaster's right during the meeting.
Kevin Kline attended Saint Louis Priory School in Missouri, a private, all-boys Benedictine high school similar to the school in the film. He drew inspiration for his performance from his experiences there, including one of his Latin teachers. His Priory ring can also be seen in the film on his left hand. After the movie came a question and answer session. One person asked Kevin if it was his ring and he said "yes." and the whole crowd cheered on.
When filming the movie, the location (Emma Willard school in Troy, NY) was still operating as a girl's school. Emile Hirsch reportedly complained about the students, claiming that they were pestering him for his phone number. He also (reportedly) said some unsavory things about the school in general. When the students heard about this, they demanded an apology from Hirsch, which he delivered in front of the entire student body. At the school viewing, whenever he appeared on screen, the girls booed loudly and stories about him still circulate through the student body.
While on location at the Emma Willard School in Troy, New York, Kevin Kline stood in as an English teacher for several classes who were studying Shakespeare at the time. Students gave him rave reviews as an instructor.
Kevin Kline was obsessed with the handwriting that was seen in the film and he wanted to do it himself which is hours that the crew didn't have. They made fun of him the fact he misspelled the word Republic.