Matt Dillon's outing of his teacher in his acceptance speech is based upon Tom Hanks' real-life acceptance speech at The 66th Annual Academy Awards (1994) for his Oscar for Philadelphia (1993), in which he thanked a gay teacher.
The Oscar statuette used in the film is Kevin Kline's. He won it in 1989 for his performance in A Fish Called Wanda (1988).
All of the high school scenes were shot at Pompton Lakes High School in Pompton Lakes, NJ. Unfortunately the school district's superintendent forgot to sign the waiver allowing the school's name to be mentioned in the credits. Other than paint, the building remains nearly identical to the way it was during filming, including the unique terraced floor in the poetry class scene.
The disco group The Village People originally would not sign off on the use of the song "Macho Man" for the film, which features the track heavily. The disco tribute band The Boogie Knights was therefore hired to record a cover version to use instead. After the cover version was completed, The Village People ultimately decided to let the filmmakers use their original version and the Boogie Knights version was never used.
Joan Cusack plays Matt Dillon's former high school teacher in this movie, even though she is only two years older than 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.
The suit Matt Dillon wears to the Academy Awards is based on the suit Brad Pitt wore at The 68th Annual Academy Awards (1996).
The "Roadhouse Bar" exterior featured in the film is The Homestead Restaurant in Sparta, NJ.
The film cast includes two Oscar winners: Kevin Kline and Whoopi Goldberg; and five Oscar nominees: Matt Dillon, Joan Cusack, Debbie Reynolds, June Squibb and Glenn Close.
Joseph Maher as Father Tim, the town's priest, from whom Howard seeks help, also plays a priest in Sister Act (1992), as Monsignor O'Hara. Whoopi Goldberg, also in Sister Act, makes an appearance at the awards show, next to Tom Selleck.
Debbie Reynolds appears in this film for director Frank Oz, who worked with her daughter Carrie Fisher in The Blues Brothers, The Empire Strikes Back, Return of the Jedi, and The Last Jedi (which also featured Reynolds's granddaughter, Billie Lourd) .
Included among the American Film Institute's 2000 list of the 500 movies nominated for the Top 100 Funniest American Movies.
Three of Brackett's (Kevin Kline) students appear in the same episode of Six Feet Under. Shawn Hatosy and Alexandra Holden (playing a couple again) and Lauren Ambrose.
The interior bar shots were filmed at Slater's Mill, a bar in Riverdale, NJ that has been closed down for quite a number of years. However it is still standing with its name painted on the building's side.
Howard (Kevin Kline) being a dedicated fan of Barbra Streisand is a recurring joke throughout the film, and in this film, Bob Newhart plays the school principal who has to decide the fate of Howard's job, amid a lot of controversy and press. In 1970 Bob Newhart played a school administrator in the Barbra Streisand film On a Clear Day You Can See Forever (1970), where he had to decide on the fate of Professor Marc Chabot's job (portrayed by Yves Montand), amid a lot of controversy and press.
Tom Selleck and Alexandra Holden both had recurring roles on Friends as Dr. Richard Burke, Monica's boyfriend and Elizabeth Stevens, Ross' girlfriend.
The podium that is used by Bob Newhart at the graduation ceremony is currently used still in a classroom today at Pompton Lakes High School, the place they used to shoot the scenes at the school.
Gregory Jbara (Kevin Kline's brother in In & Out) later stars with Tom Selleck again in the TV drama Blue Bloods (2010).
Deborah Rush (Ava Blazer) & Bill Hoag (Bartender) also worked together on Orange Is the New Black (2013) as Carol Chapman & Bill Chapman respectively.
Selma Blair appears with Howard's family for the awards show, as well as at the wedding.