The high school scenes were mostly shot at Pompton Lakes High School, yet the school and town receive no mention in the closing credits. This is due to the School's Superintendent forgetting to sign the waiver allowing the school's name to be placed in the credits.
Joan Cusack plays Matt Dillon's former high school teacher in this movie, even though she is only two years older then he is and they played classmates and age contemporaries in My Bodyguard (1980). She states she was a student teacher when she helped him in school, which could explain how they could be close in age.
Joseph Maher as Father Tim, one of the town's priests from whom Howard seeks help also plays a priest in Sister Act, as Monsignor O'Hara, also Whoopi Goldberg also makes an appearance at the awards show, next to Tom Selleck.