- Creepy Awesome: Vicky is a borderline sociopath, and an awesome girlfriend.
- Critical Dissonance: As usual for Sandler, the film was slammed hard by critics but was a huge hit with audiences.
- Ensemble Dark Horse:
- Fetish Retardant: Vicky's enormous, cigarette-stained teeth. Justified in Fairuza Balk has built a career out of these kinds of scary hot roles.
- Hilarious in Hindsight: During the instant replay of Bobby's tackle, you can hear his opponent cry out "My leg!"
- Jerkass Woobie: Helen "Mama" Boucher, who smothered Bobby so much out of pain over her husband and Bobby's father abandoning them. You can see and feel the pain as she mouths the words "And a voodoo woman named Phyllis" from her husband's breakup note. To make it worse, Helen was still pregnant with Bobby when her husband left. After all this comes to light, she starts to redeem herself in the third act.
- Memetic Mutation: "Waaaaaaaaater sucks! It really, really sucks! Waaaaaaaaaater sucks! It really, really suuuuuuucks, suuuuuuuuuuuucks, suuuuuuuuuuuucks!"
- "Gayyyy-tor-raaaade!" "H2O"!
- "You can do it!"
- "Memes are the debil!"
- One-Scene Wonder: Paul Wight, aka The Big Show, as "Captain Insane-O", who laughs so hard at the thought of 31-year-old Bobby being his waterboy that he cries.
- The Woobie:
- Bobby spent his whole life taking so much crap from everyone, that it shouldn't be surprising that there's so much built-up rage which helps him play football.
- Coach Klein, who went from brilliant assistant coach to a borderline Cloud Cuckoolander after Red Beaulieu stole the playbook he spent years making, so he could become head coach rather than Klein.
YMMV / The Waterboy