|Billy Madison (1995)
Starring: Adam Sandler, Bridgette Wilson, Bradley Whitford, Darren McGavin, Josh Mostel, Norm Macdonald
Director: Tamra Davis
First, he was Opera Man, Canteen Boy and Cajun Man. Then, he was Billy Madison. Riding a swelling wave of popularity from his five years on "Saturday Night Live," Adam Sandler co-wrote and starred in "Billy Madison" in 1995, a comedy about a 27-year-old slacker in desperate need of a kick in the pants. That kick is eventually delivered by Billy's father, hotel tycoon Brian Madison (Darren McGavin), who threatens to hand his empire over to vice president Eric Gordon (Bradley Whitford) if Billy doesn't pull his life together.
To prove that he's responsible enough to inherit his father's company, Billy agrees to go back to school and complete grades one through 12, the grades he originally passed only because Mr. Madison paid off Billy's teachers, within six months. Along the way he meets several helpful elementary school kids, a gay principal who once made a living as a pro wrestler (Josh Mostel), a deranged school bus driver (Chris Farley), and the scrumptious Ms. Veronica Vaughn, Billy's third-grade teacher, played wonderfully by Mrs. Pete Sampras, Bridgette Wilson.
It's not the most complicated story out there, and it's certainly not the most mature selection you're going to find on the Blockbuster shelves, yet somehow Sandler and the rest of the cast make it work. Billy is instantly lovable and the villain, Whitford's Eric Gordon, is just as detestable, and if a film genuinely has you rooting for the good guy and against the bad guy, then it's doing something right. Add to that a script full of successful jokes and memorable scenes like Billy's hilarious dodgeball game on his first day of school, and you've got a movie that's funnier than it should be.
For many of us, films like "Billy Madison" rank near the top of our 'guilty pleasures' list. Is it sophomoric? Yes. Is it silly? Absolutely. Is it stupid? On more than one occasion. But it's also funny and, some would argue, even endearing.