Billy Madison

Billy Madison (Adam Sandler), the 27-year-old scion of the esteemed Madison Hotels empire, has spent his entire life indulging in the luxuries afforded by his family's vast fortune. With 650 properties under their belt and a workforce of over 61,000 employees, Billy's existence has been one of perpetual pampering. His days are filled with drinking binges alongside his cohorts, Jack (Mark Beltzman) and Frank (Norm Macdonald), and causing chaos throughout his father's estate. Soaked in the sun and fueled by substances, Billy is convinced that penguins are hot on his heels, driven to capture them and relocate them to colder climates.

The steadfast Juanita (Theresa Merritt), the Madison family's trusted house maid, has been a constant presence in Billy's life, offering a sense of stability amidst the chaos. However, her efforts are put to the test when Billy's antics reach new heights. His father, Brian (Darren McGavin), has had enough of his son's irresponsible behavior, and tensions come to a head during a dinner meeting with high-ranking business associates.

Billy's tardiness and subsequent outbursts, egged on by Eric Gordon (Bradley Whitford), Brian's executive vice president, prompt the elder Madison to lose faith in his son. In a shocking turn of events, Brian announces that he has chosen Eric as the next CEO of Madison Hotels, effectively passing over Carl, a loyal employee of 25 years' standing.

Brian reveals to Billy that he and his late wife had always intended for their empire to pass into Billy's hands, but Eric raises concerns about the potential impact on the company's employees. Billy, incensed by Eric's smugness, protests his father's decision, only to be met with a surprising revelation: Brian had secretly bribed Billy's teachers throughout his academic career to ensure his passing.

With his inheritance hanging in the balance, Billy is given an ultimatum: he must complete elementary school education (grades 1-12) within a span of 24 weeks, two weeks per grade. Billy's journey begins with Miss Lippy (Dina Platias), his first-grade teacher, where he struggles to master basic skills and learns to navigate the challenges of dodge ball.

As Billy navigates this uncharted territory, he faces numerous setbacks, from difficulties with hand-eye coordination to his inability to fit into the urinals designed for his young classmates. Despite these obstacles, Billy perseveres, eventually passing each grade level with flair, culminating in a grand celebration at his mansion for all his fellow students.

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As Rollo brings news of Billy's academic progress to Eric, it becomes clear that Billy has successfully navigated 2nd grade after impressing Veronica Vaughn (Bridgette Wilson), his third-grade teacher, with his exceptional spelling skills. Initially, Veronica finds Billy's enrollment a distraction for her other students, but he soon wins her respect by defending his friend Ernie (Jared Cook) from bullying. When Eric faces embarrassment during a class trip, Billy cleverly saves him from ridicule by pretending to find peeing one's pants cool, and the entire class follows suit. As Billy becomes more popular among his peers, he finds himself torn between his admiration for Veronica and the affections of the pretty girls in school.

As Billy advances through school, he begins to feel a pang of nostalgia for his third-grade days. Meanwhile, his relationship with Veronica blossoms, and they find common ground despite their initial differences. However, just as things are looking up, Carl warns Billy that Eric is plotting something. Little does Billy know, his troubles have only just begun.

As Billy navigates the challenges of high school, he's forced to confront the harsh realities of being a "cool guy." Realizing how it feels to be on the receiving end of bullying, Billy reaches out to an old classmate, Danny McGrath (Steve Buscemi), and apologizes for his past behavior. Danny accepts his apology and crosses him off his list of people to target.

Eric's frustration with Billy's progress grows, leading him to take matters into his own hands. He visits Max Anderson (Josh Mostel), Billy's grade school principal, and threatens to reveal a dark secret from Max's past as a professional wrestler. Eric coerces Max into making a damaging public statement about Billy, claiming that he bribed his way through school.

This devastating revelation sends Billy reeling, causing him to abandon his academic pursuits and revert to his carefree lifestyle. However, Veronica and others rally around him, convincing him to pick up the fight against Eric once more. With newfound determination, Billy returns to school and redoubles his efforts, realizing that reclaiming the hotel chain is crucial to restoring his sense of self-worth.

As Veronica cleverly incentivizes Billy's academic progress by removing one article of clothing for each correct answer, she inadvertently sets the stage for a thrilling climax. Meanwhile, Brian and Carl Alphonse (Larry Hankin), a stalwart Madison Hotels employee, passionately argue to Eric that Billy deserves a second chance, but their efforts are met with resistance from the skeptical hotel magnate. Unfazed, Billy decides to challenge Eric to an academic decathlon, with the winner determining his father's successor.

As the competition unfolds, both Billy and Eric showcase their exceptional skills in various events, with Billy ultimately taking a narrow lead heading into the final round – a high-stakes Jeopardy!-style test. Eric seizes the opportunity to answer and potentially claim victory, but his confidence is shattered when he's faced with a question on business ethics, an unfamiliar terrain that leaves him reeling.

In a last-ditch effort to salvage his dignity, Eric brandishes a gun at Billy, only to be swiftly subdued by Max, who appears in his wrestling attire. Despite this setback, Eric's determination to exact revenge on Billy knows no bounds, and he attempts to turn the tables by targeting Veronica with his firearm. However, just as all hope seems lost, Danny McGrath materializes with a high-powered rifle and disarms Eric with a well-placed shot to his behind.

As the dust settles, Billy takes a moment to celebrate his graduation and announces that he will be passing on the family business to Carl, opting instead to pursue higher education and realize his dream of becoming a teacher.