Happy Gilmore (1996)
Sure, some may claim that Billy Madison (1995) was the film that introduced Sandler’s specific brand of charisma to the world, yet Happy Gilmore was the one that truly wedged itself into public consciousness. Aside from the fact that it’s the superior of the two films – more confident in its own silliness, better acted and shot – HG confirmed that Sandler’s somewhat dim-witted, “prone-to-violent-anger-yet-lovable-and-exceptionally-skilled-at-something” hero resonated with the everyman, big-time. It made over $40M on a $12M budget and only kept gaining popularity on VHS. The critics did not respond so kindly. “Tells the story of a violent sociopath,” Roger Ebert wrote. “Since it’s about golf, that makes it a comedy.” That disparity between fan adoration and critical hatred has since defined the majority of Sandler’s career. HG marked the beginning of a beautiful partnership between him and director Dennis Dugan (they’ve made at least seven features together since, including their funniest, 2008’s You Don’t Mess with the Zohan) and paved the way to superstardom.
“…’prone-to-violent-anger-yet-lovable-and-exceptionally-skilled-at-something’ hero resonated with the everyman, big-time.”
The Wedding Singer / The Waterboy (1998)
If Happy Gilmore put Sandler on the map, the one-two punch of Frank Coraci’s The Wedding Singer and The Waterboy established the training-pants-wearing actor as a bona fide star. He effortlessly wooed Drew Barrymore’s heart (as well as ours) in the former and kicked a*s on the football field (despite alleged mental impairment) in the latter, raking in circa $300M at the box-office in the process. Critics argued that his fare was borderline-offensive, relied heavily on slapstick, and followed the oldest tropes in the book. Fans saw an underdog in Sandler that they found easy to root for; the slapstick gave them leeway to switch off brains without the hangover of guilt, and the tropes wrapped it all in a cozy blanket of familiarity. Coraci (Click, Zookeeper) and Fred Segal (Anger Management, 50 First Dates, The Longest Yard) consequently joined Dennis Dugan as Sandler’s go-to helmers.