The movie is based on the personal experiences of writer and television producer Dick Wolf.

The campus scenes in the movie were shot at Middlesex School in Concord, Massachusetts. When the school offered their school for the campus scenes, they were not aware of the plot.

Several places in Groton, Massachusetts, were given money to fix up their building in order to be in the movie.

The Scranton Bus Depot scene was filmed outside Russell's Package Store in Leominster, Massachusetts. The building was a former train station, and the exterior looked like an old bus station. The owners were compensated for its use with a complete interior remodel. To this day, the Scranton, Pennsylvania Bus Depot decals remain in the front windows of the liquor store.

While reviewing this movie on his show, Gene Siskel recalled experiencing anti-Semitic prejudice during his time at prep school, including being handed piece of toast with jam in the shape of a swastika. Siskel said the film had a fairly high bar with him due to its subject matter, but the end result pleased him very much.

Ironically, considering the students' pervasive anti-Semitism, "Smokey Joe's Café", the song that the classmates enjoy (and which Mr. Cleary dismisses as being from the "jungle") was written by Jerry Leiber and Mike Stoller, a pair of Jewish songwriters, who wrote many of the biggest radio hits of the 1950s and early 1960s. Many of the other songs in the movie and on the soundtrack were also written or co-written by Jewish songwriters, including "Rock Around the Clock", "Three Coins In The Fountain", "That Old Black Magic", "Isn't It Romantic", and "When I Take My Sugar To Tea."

David's football number is 42, and Charlie's number is 21, implying that Charlie is half the man that David is.

Matt Damon remembered Director Robert Mandel trying to lift the young actors's spirits by telling them that they were going to be "the next big thing, the next Brat Pack", referring to the regular ensemble John Hughes used during his films in the 1980s. Ben Affleck, Matt Damon, Brendan Fraser, and Chris O'Donnell all became major movie stars.

The French assignment that McGivern fails to recite properly is a French translation of the poem "On Seeing the Elgin Marbles for the First Time," by John Keats.

David's number is 42, the same as baseball's Jackie Robinson, who himself suffered extreme racism and discrimination as Major League Baseball's first African American player.

Cole Hauser's film debut.

The Hebrew prayer that David recites in the chapel is the "Avenu Malkenu" (literally, "Our Father, Our King"), which is a series of petitions to God to grant atonement. The prayer is repeated throughout the High Holy Days, ten days starting with Rosh Hashanah, the New Year in the Jewish calendar, and ending with Yom Kippur, the Day of Atonement. David misses Rosh Hashanah services because of the football game.

Matt Damon, Ben Affleck, and Cole Hauser appeared in Good Will Hunting (1997).

The marching band in the film is from Westford Academy, in Westford, Massachusetts. One of the bass drum heads from the movie, signed by the cast and crew, is on display in the school's music department.

In interviews, Brendan Fraser said the production crew ran out of hot water while the shooting the shower fight. Much of that scene was shot using cool water.

Amy Locane and Brendan Fraser also played a couple in Airheads (1994).

John Cunningham also played Matt Damon's father in Mystic Pizza (1988).

In the French version, Le College d'Elite, all the scenes with the obnoxious French teacher, Mr. Cleary, who keeps riding MCGiven, were changed to an Italian teacher. All the dialogue in French was dubbed in Italian. The name of the absent French teacher, Monsieur Renard, was changed to Signore Rinaldi.

The gym scenes were shot at Worcester Academy, in Worcester, Massachusetts.

Ben Affleck, Randall Batinkoff, and Andrew Lowery all appeared in Buffy the Vampire Slayer (1992).

Iselin Hall, where Greene says he will meet whoever made the sign with the swastika, is named after John Iselin, the Communist-hunting Senator in The Manchurian Candidate (1962),

The Skip's Blue Moon Diner scene was filmed in Gardner, Massachusetts.

Cole Hauser,Ben Affleck, and Anthony Rapp appeared in Dazed and Confused (1993).

A night practice scene got cut after several re-shoots, due to tensions between the African-American players and the Caucasian players. After the director gave permission to the actors to actually hit each other, a fight broke out on-set, with Brendan Fraser and Matt Damon caught in the crossfire. The scene was shot in Twentynine Palms, California.

Maurice Jarre also composed the score for Dead Poets Society (1989). Jarre's elegant melodies personify youthful alienation due to parental expectations, as well as parental prejudices.

The same year this film was released, Ben Affleck, Matt Damon, Brendan Fraser, Chris O'Donnell, Cole Hauser, Anthony Rapp, and Randall Batinkoff tested for the role of Charlie Simms in Scent of a Woman (1992).

Parts of the film were shot in Lowell, Massachusetts.

Cole Hauser also played a bigoted role in the movie Higher Learning.

Matt Damon's character is named after one of Casting Director Lisa Beach's classmates.

Brendan Fraser played George of the Jungle (1997) 5 years later.

Brendan Frasier wears number 42 in the movie. This is the same number worn by Sid Luckman, a Pro Football Hall of Fame quarterback, who wore the number in college at Columbia and in the NFL for the Chicago Bears. Luckman was also Jewish.

John Cunninghams character's first name is Grayson. In Batman Forever (1995) and Batman & Robin (1997), Chris O'Donnell's character's last name is Grayson.

Zeljko Ivanek and Ben Affleck appeared in Argo (2012).

Ben Affleck and Chris O'Donnell would go on to play Batman and his sidekick Robin, respectively, in different films.

In real life, Matt Damon and Ben Affleck are good friends.

Ben Affleck plays Bruce Wayne, a.k.a. Batman, in the DC Extended Universe.

Matt Damon, Chris O'Donnell, and Ben Affleck all went on to play lawyers in their later roles. O'Donnell appeared in The Chamber (1996), Damon in The Rainmaker (1997), and Affleck in Daredevil (2003). Daredevil was the only one of those films not based on a novel by John Grisham.

At the end, Matt Damon's character says "I'm still gonna get into Harvard, and you'll still be a God Damn Jew." Damon went to Harvard in real life.

In this film, Brendan Fraser's character wants to go to Harvard. In With Honors (1994), he plays a guy who goes to Harvard.