The first “real” Adam Sandler movie, released during his final season as an SNL cast member, has the kind of surefire premise that has nonetheless failed to save many a comic vehicle: Sandler plays a spoiled rich idiot who agrees to repeat his entire K-12 education to prove he’s got what it takes to run his dad’s company. Is this movie why so many of Sandler’s other films have centered wealth, even before he became filthy rich himself? In any event, Billy Madison remains a deeply silly, crude, and surprisingly whimsical comedy 30 years later, with the neat bookend in the form of Sandler’s recent Netflix cartoon Leo. There, rather than speed-running through the grades, Sandler’s titular lizard stays in the same fifth-grade classroom for decades, passively absorbing life rather than participating in it. When kids start bringing the lizard home on the weekends as an exercise in responsibility, he starts counseling them (much as Billy does, more on the fly, in the earlier movie), and Leo turns out to be a perceptive and funny movie about teaching. Robert Smigel, in what will not be his final appearance on this list, co-writes and co-directs, and his satirical fingerprints are all over this cartoon musical, which goofs on overprotective parents and rich jerks alike.
3. The Master of Ceremonies: The Wedding Singer (1998) and The Week Of (2015)
Macall Polay/Netflix
As befits a star of his magnitude, Adam Sandler has landed plenty of talented women as his co-stars, often playing his love interest or, in later movies, his wife. Yet chemical reactions don’t come easily to him on the big screen; performers as varied and charismatic as Marisa Tomei, Salma Hayek, Kate Beckinsale, Patricia Arquette, and Rosemarie DeWitt have failed to strike much of a spark. A few stronger co-stars have emerged: Emily Watson, by dint of her strengths as an actress and the nature of the movie she made with Sandler; Jennifer Aniston, by businesslike default as much as anything; Winona Ryder, for a few moments of Mr. Deeds. But the one co-star who really vibes with Sandler in a romantic way is Drew Barrymore. They just get each other; she teases out his sweetness and he keeps her smiling. They’ve made three together; their first, The Wedding Singer, is such a natural blend of then-nascent Sandler blueprints with rom-com formula that it’s no wonder they reunited twice afterwards, to lesser effect. There’s something about the wedding setting—packed with familial bonds, obligatory oddballs, and ceremony that can be comically undermined—that works well with Sandler, as he showed years later in a very different part, playing father of the bride (in the Steve Martin sense) for The Week Of. It’s ostensibly an uneasy buddy comedy between Sandler and father of the groom Chris Rock, and that stuff mostly works, but writer-director Robert Smigel seems just as interested in celebrating the hustle, bustle, and eye-rolling of a Long Island family get-together. And Sandler has a funny and age-appropriate on-screen spouse in the form of the wonderful and frequently underappreciated Rachel Dratch, a pairing that makes it seem like he wasted a lot of time in the interim years, chasing after bigger, more glamorous stars just to underuse them. Why hasn’t he always been paired with SNL ladies when Drew isn’t available? Shouldn’t Sarah Silverman have been in one of these things by now?
2. The Dark Side: Funny People (2009) and Uncut Gems (2019)
A24/Everett Collection
