University of Toronto trademarked the name Varsity Blues for its sports teams in the mid 1980s. U of T complained the movie presented sports in a negative light, and sued Paramount Pictures, settling for an undisclosed amount and setting up eight scholarships for academically accomplished student athletes.
The announcers weren't real actors. The announcers called local high school games in Texas. In fact, the announcers called a high school game in Texas that was labelled " the greatest high school comeback ever" between Plano East and John Tyler, in 1994.
All the beer in the movie, though it appears to be Budweiser, is actually just labelled "Beer". However, in the barbecue scene, you can clearly see that the can Lance's (Paul Walker's) father puts on his head is labelled "Lonestar", an actual beer that is popular in Texas.
The scene in which Ali Larter appears basically naked but for the "whipped cream bikini" is generally regarded as the film's most iconic scene and possibly the most iconic moment of Ali Larter's career.
On the trailer for this film there are several scenes that never appear in the movie. For example, there is a clip with Jules (Amy Smart) tells Mox (James Van Der Beek): "You woke up in the twilight zone....West Canaan, sex, and football. That's all there is." Another scene where a girl in the pep-rally asks Lance (Paul Walker) to sign her buttocks also never appears.
Plans for a television series based on the movie were planned. The series also was going to feature Ron Lester reprising his role as Billy Bob. But for unknown reasons the plans never got past the pilot episode.
The gentlemen's club (The Landing Strip) seen in the film is located east of downtown Austin off the Bastrop Freeway (U.S. Highway 183) north of State Highway 71 adjacent to Austin-Bergstrom International Airport. Another Austin landmark seen in the film is Top Notch Burgers located off of Burnet Road in north Austin.
Ron Lester's character "Billy Bob" has no apparent last name. He is only referred to as Billy Bob or William Robert by all other characters in the movie, and he is the only player on the Coyotes' team to have no last name on the nameplate of either his youth football jersey or his varsity high school jersey. In both cases, the name on his back is simply "Billy Bob".
In 2019 the FBI charged some 50 people (including several celebrities) with conspiracy to fraudulently influence academic and athletic admissions decisions at several elite colleges and universities. Multiple news outlets (including The New York Times, The Washington Post, NBC, CBS, ABC, CNN, The Guardian, etc.) reported that the FBI's internal codename for the investigation was "Operation Varsity Blues," after the 1999 movie. One of that movie's stars, James Van Der Beek, tweeted a wry response to the scandal and its name: "If only there was a succinct turn of phrase these kids could have used to inform their parents they were not desirous of their life path..." This is a joking reference to the dramatic moment in the movie in which Van Der Beek's character in the movie, Mox, tells his father, "Playing football at West Canaan may have been the opportunity of your lifetime, but I don't want your life!"
The practice field where Moxon tries to run the oompty-oomp play was the practice field for the Taylor, Texas High School Duck football team. As of this date, August 7, 2016, the Taylor Ducks no longer use this location, as they now practice at the new high school that opened in 2011. Additionally, the open fields seen in this scene are now gone, replaced by a large housing subdivision.
When the Coyotes return to the field for the second half of their divisional championship game without Head Coach Kilmer, they are coaches by a hobbled Lance Harbor. During this sequence, not only is there no sign of Coach Kilmer, but of any other assistant coach as well. In today's actual high school games, this scenario would not be allowed to unfold, as most, if not all high school state football alliances, require teams to have a certified and state registered coach on the sidelines during all games.