Burt Reynolds was supposed to have a stunt double for when he got hit by Brian Bosworth on a touchdown run, but Reynolds insisted on doing it himself, saying "I got one run left in me." Bosworth himself was flattered by the whole situation, saying "Who else can say they got run over by Burt Reynolds?" Reynolds went through the hit in one take with no injuries, though he had to be helped off the field.
Michael Papajohn who plays Guard Papajohn, was Adam Sandler's stuntman in The Waterboy (1998), making the hard hits as Bobby Boucher. In The Longest Yard, things came full circle as Michael has his own stuntman.
The movie was filmed in a closed down part of the New Mexico State Penitentary called "Old Main". It was this part of the prison where one of the worst prison riots in U.S. history occurred on 2 February 1980. The state offers the building for rent for film purposes.
Crewe mentions a "tune-up" game in which he states "In college, we'd start every season against Appalachian State or some slack Division II team. Kick the living shit out of them." Two years after this movie was released, Appalachian State went on to win 3 National Championships in a row in Division IAA as well as defeating then number 5-ranked Michigan in a "tune-up" game.
Michael Irvin played a practical joke on Bill Romanowski while filming a scene in the locker room. Irvin replaced the fake, collapsible locker door that Romanowski head butts with a real, solid locker door. This can be seen as an outtake on the DVD.
Adam Sandler's character (Paul Crewe) was supposed to have played college football for Florida State Univesity and Pro football for Pittsburgh. Burt Reynolds, who starred in both films, was an All-American running back at Florida State and is an avid Pittsburgh Steelers fan.
While many of the inmates are seen with long hair and/or facial hair, in reality the Texas Department of Criminal Justice requires inmates to be clean shaven and their hair "trimmed from the back of the hair and necks," essentially ensuring everyone is bald and beardless. Smoking has also been in Texas prisons strictly forbidden since 1994.
Filming of the football game occured during El Camino College's fall semester. As a result, the stadium set stayed up during El Camino's home football games. Some of the extras in the crowd during the stadium scene are El Camino College students.
In the scene where Meggett (Nelly) "runs" out of his shoes in his first practice, the camera pans over to Caretaker (Chris Rock) and Coach Nate Scarborough (Burt Reynolds) and a convict is seen approaching to get a better look. The convict is former University of Texas running back Ricky Williams.
Chris Berman's play call of "Look at that little Meggett run!" is a reference to a famous NFL Monday Night Football (1970) incident. Howard Cosell's original call of "Look at that little monkey run!" in describing Washington Redskin Alvin Garrett sparked a controversy and accusations of racism because Garrett was black. Berman even tries to imitate Cosell's voice on the call. Berman also used this line and voice on ESPN when describing the play of former New York Giants running back Dave Meggett.
The song "Saturday Night Special" By Lynyrd Skynyrd appears at the start of both the original and the remake. Also, as in both the original and the remake, Crewe is watching a football game right before the argument with his girlfriend, though unlike the original Crewe does not strike his girlfriend, he merely locks her in the closet.
When Knauer is escorting Crewe through the prison yard, he mentions he played college football at the U of Miami, and mentions that none of the inmates are former teammates, but some of the guards are.
In the late 80's there was a brief rivalry between the U of Miami and Notre Dame, and is was billed as "Catholics vs. Convicts"
While sharing a drink, Caretaker (Chris Rock) tells Crewe (Adam Sandler)''When I get outta here, I don't want you to go all Hollywood on us...''which is funny because Chris Rock's and Adam Sandler's next project together was Grown Ups (2010) where Sandler's character is nicknamed Hollywood because he's a big time agent.
During the final play of the first half, as the Mean Machine keeps doing laterals, Chris Berman at one point cries out, "Shades of Cal-Stanford!" Berman is referring to The Play between California and Stanford in 1982, when California did several laterals on the last play of the game to win the game over Stanford.
The original 1974 film was solely released by Paramount. Columbia's involvement in the remake came because Adam Sandler was to be the film's star. Columbia has released most of Sandler's films since 2000.
After Paul Crewe (Adam Sandler) comes back in after having betrayed his teammates the O-line doesn't block the guards. On the second sack, guard Lambert (Bill Romanowski) spits on Crewe as he's getting off of him. In real life Romanowski, an NFL linebacker with the San Francisco 49ers, Philadelphia Eagles, Denver Broncos and Oakland Raiders from 1988 to 2003, (at the time a Bronco) spit in the face of 49ers' WR J.J. Stokes.
In the scene where Capt. Knauer (William Fichtner) is escorting Crewe to the Warden's office, he mentions playing for the University of Miami, one of the top collegiate football programs in the nation. Michael Irvin, who plays Deacon Moss, played football for the University of Miami as a wide receiver from 1984-87 winning the National Championship in 1987 among setting other school records.