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  • Accidental Aesop: The standard "Be Yourself" aesop slips in with minimal fanfare. Billy effortlessly connects with the elementary school kids because he's essentially an 8-year-old in a man's body. When he starts going to school with teenagers, he puts way too much effort into trying to be cool and is either avoided or mocked for it.
  • Alternative Character Interpretation: Was Carl trying to get Billy to be president because he knew he'd be the real power behind Madison Hotels and knew that if Eric took charge, he'd be powerless?
  • Big-Lipped Alligator Moment:
    • There is a solitary musical sequence in the middle of the movie containing several of the film's characters.
    • Additionally, the "Schlopppy Joes" scene. Even with vaguely dramatic music playing in the background, it adds nothing to the plot.
    • Billy dancing to "I'll Tumble 4 Ya" on the stairs.
  • Critical Dissonance: Like many of Adam Sandler's movies, this movie was slammed hard by critics, but was a huge hit with audiences.
  • Ensemble Dark Horse:
    • Chris Farley as the bus driver due to his quotability.
    • Danny McGrath, the man who Billy apologizes to for having bullied him in the past. That scene, along with Danny saving Billy from a gun-toting Eric, is considered among the best in the film for being a humanizing depiction of bullying and being a source of Character Development for Billy.
  • Fountain of Memes: The bus driver simply because how hammy he is.
  • Fridge Brilliance: See here.
  • Fridge Horror: See here.
  • Harsher in Hindsight:
    • In the opening scene, Billy gives a warning about UV rays and applies sun lotion. Theresa Merritt, who played Juanita, died from skin cancer a few years later.
    • Eric bringing a gun into a school and threatening an entire auditorium is wildly uncomfortable post-Columbine and remains so as more and more school shoot-ups continue to occur throughout the 21st century.
    • On a similar note, Danny has an "enemies list" and can shoot anyone who crosses him. This is a more uncomfortable reality with the rise of mass shootings.
    • The dodgeball scene becomes less funny when you find out that Adam Sandler actually did throw dodgeballs at those kids, and their reactions to getting hit were genuine. The director has said that she had to cut away after the kids started crying.
    • Billy's father bribed his teachers to let him pass school. The recent scandals involving wealthy people bribing admissions officers reveals how much corruption there is in American education.
    • Eric's inability to answer a question about business ethics is pretty hilarious. But the Enron scandal and the Great Recession have proven that American entrepreneurs also behave unethically.
  • Hilarious in Hindsight:
  • Memetic Mutation:
    • "YOU BLEW IT!"explanation
    • Images and video of the Principal giving his "The Reason You Suck" Speech to Billy after his crazy answer are often used as reactions to something stupid.
    • Images of the Bus Driver seething in anger after the kids throw the sandwich at him and he threatens to turn the bus around are a popular reaction image on social media.
  • Moral Event Horizon: Eric himself starts out as typical corporate sleaze. But then he basically blackmails Billy's prinicipal into failing him anyways. When Eric tries to shoot Billy. After the Principal intervenes, he tries to shoot Veronica For the Evulz.
  • Once Original, Now Common: While the "man-child who has to prove himself" comedy today is extremely played out and is getting close to being a Dead Horse Trope, in the early 90s, this premise was actually considered a risky venture due to its untested appeal. And while Adam Sandler today is known for these things, this was his first lead role (aside from a movie he (and likely many others) would like you to forget ever existed), so his bankability and brand of humor were unknowns. The studio was unsure how much faith to even place in the film until test audiences loved it.
  • Retroactive Recognition: If you were a kid in the 90s, odds are this was your first Steve Buscemi film.
  • Signature Scene: The "everyone is now dumber" rant.
  • Signature Song: “The Stroke” by Billy Squier.
  • Squick: The MILF that one of Billy's friends is eyeing off blows a kid's nose, sees him making eyes at her and seductively caresses her neck and cleavage, obviously forgetting that she still had a snotty tissue in her hand.
  • Unintentional Period Piece:
    • Seeing a high school without kids on their smartphones or laptops thoroughly places this movie in the 1990s, before ownership of cell phones and computers went mainstream.
    • Billy talking about how good of a game Donkey Kong makes sense for a young adult in the 1990snote  but not for a young adult in the 2020s.
  • Values Dissonance: Since this is a film in the 1990s, there were jokes made at this time that would simply not fly today.
    • Principal Anderson's homosexuality is only made clear by having him make creepy advances on Billy. Such portrayals nowadays would be considered undeniably homophobic, and the fact that Anderson is Hot for Student (albeit a grown man) is what should come across as questionable.
    • Billy's not-so-Accidental Pervert moment with Veronica is still Played for Laughs even though he outright tells his classmates it's sexual assault. The fact that Veronica doesn't hit him or report comes across as jarring considering she is supposed to be a take-no-shit woman who helps him grow up. She's apparently brushed it off as a "shit happens" kind of thing.
    • Although it can be seen as badly needed Tough Love and a Get A Hold Of Yourself Man moment, Veronica gets Billy back on track by beating him up (which he thanks her for) and attempting to drown him.
    • Eric pulling out a handgun and threatening the school is treated as a hilarious Villainous Breakdown. The epidemic of school shootings make this moment a lot more scary than funny. For that matter, Billy's former classmate crossing him off the hit list and saving him at the end also likely wouldn't fly today, as well as his habit for putting on lipstick being used to mark him as creepy.
    • Billy making a joke about how he wants to make out with one of his teenage classmates is far more repugnant than funny.
  • Values Resonance: In the movie, bullying is rightfully portrayed as a cruel act that isn't OK.
    • Veronica immediately tells off Billy for making fun of a kid who struggles with reading. Billy takes that lesson to heart and saves one of his younger classmates from embarrassment, which is one of the moments where he begins to grow as a person.
    • Billy and his high school friends endure a lot of mistreatment from their peers and this isn't played for laughs either.
    • Billy decides to call Danny, a former childhood classmate, and apologises to him for the years of bullying that he put him through. While there's still some Black Comedy with Danny removing Billy's name from his hit list, the film not only treats the apology as a sincere moment of growth for Billy, but it also inadvertently saves his life when Danny later shows up and shoots Eric to protect him. With bullying and its long-term effects gaining greater awareness in recent years, this scene has become surprisingly poignant.
    Billy: I'm glad I called that guy.

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