History Trivia / TheWaterboy

** The movie was initially conceived as a 1950s period piece taking place in New England shot in black-and-white, before making it a present-day piece in Louisiana because Sandler.

* AsHimself: Every time an NFL or NCAA football personality (whether it be player, coach, or commentator) that exists in real life appears, they are played by the actual person, including (but not limited to) Lynn Swann, Dan Fouts, and Lawrence Taylor.
* CareerResurrection: Prior to this movie, Creator/HenryWinkler was still living in the shadow of [[Series/HappyDays Fonzie.]] After ''The Waterboy'' came out, Winkler gained new appreciation from a younger generation that did not grow up watching ''Happy Days'' (if they were even alive when it originally aired), allowing him to have a respectable career as a character actor, and an Emmy-winner to boot.

* PlayingAgainstType: Creator/HenryWinkler (AKA [[Series/HappyDays Fonzie]], the coolest of cool) plays a loser coach.
** However this seems to be more in line with the roles Winkler currently gets.
* SoMyKidsCanWatch: Creator/KathyBates was convinced to take the role of Helen "Mama" Boucher by her niece, a longtime fan of Creator/AdamSandler.

* ActorAllusion: Vicki Vallencourt is into astrology, and at one point, Mama Boucher says to Bobby "come on inside before that little ol' witch cast a spell on you." Creator/FairuzaBalk, who plays Vicki, played a witch who'd cast spells in ''Film/TheCraft''.
* PlayingAgainstType: Henry Winkler (AKA [[Series/HappyDays Fonzie]], the coolest of cool) plays a loser coach.

* PlayingAgainstType: Henry Winkler (AKA Fonzie, the coolest of cool) plays a loser coach.

* PlayingAgainstType: The coolest of cool Fonzie plays a loser.

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* This movie is on the infamous RogerEbertMostHatedFilmList.

* HeyItsThatGuy: [[HappyDays The Fonz]] as Coach Klein.
** Wrestling/TheBigShow, or [[Wrestling/{{WCW}} The Giant]], as he was known as back then, as Captain Insano.
** And, of course, Rob Schneider as the Townie.
** [[Series/TwoAndAHalfMen Chelsea Milini]] is Rita, the girl who flirts with Bobby at a post-game party.
** [[{{Film/Misery}} Annie Wilkes]] is Bobby's mama, no wonder everyone's scared of her.
** [[Series/TheWalkingDead Bob Stookey]] is the Mud Dogs kicker, which arguably becomes HilariousInHindsight or HarsherInHindsight for those who have seen ''Series/TheWalkingDead''.

** [[Series/TheWalkingDead Bob Stookey]] is the Mud Dogs kicker, which arguably becomes HilariousInHindsight or HarsherInHindsight for those who have seen TheWalkingDead.

* PlayingAgainstType: The coolest of cool Fonzie plays a loser.

** [[Wrestling/{{WWE}} The Big Show]], or [[{{WCW}} The Giant]], as he was known as back then, as Captain Insano.

** [[Series/TheWalkingDead Bob Stookey]] is the Mud Dogs kicker, which arguably becomes HilariousInHindsight for those who have seen TheWalkingDead.

** [[Series/TheWalkingDead Bob]] is the Mud Dogs kicker, which arguably becomes HilariousInHindsight for those who have seen TheWalkingDead.

** [[ TheWalkingDead Bob]] is the Mud Dogs kicker, which arguably becomes HilariousInHindsight for those who have seen TheWalkingDead.

** [[ TheWalkingDead Bob]] is the Mud Dogs kicker, which arguably becomes HillariousInHindsight for those who have seen TheWalkingDead.

** [[{{Film/Misery}} Annie Wilkes]] is Bobby's mama, no wonder everyone's scared of her.

** [[{{Misery}} Annie Wilkes]] is Bobby's mama, no wonder everyone's scared of her.

** [[Series/TwoAndAHalfMen Chelsea Milini]] is Rita, the girl who flirts with Bobby at a post-game party.