10. Hal L.
Happy Gilmore (1996)
“Check out the name tag. You’re in my world now, Grandma.” And so we’re introduced to Stiller’s Jekyll-Hydian Hal L., the nefarious orderly who turns the nursing home of Happy Gilmore’s sweet grandma into a godless sweatshop. What separates Hal from Stiller’s litany of abusive weirdos is both physical AND performative: the horseshoe ‘stasche, for one, deftly conveys unhinged masculinity, while his threatening demands resonate more as a twisted middle-management tactic than anything genuinely dangerous. Perhaps most importantly, Hal L. is probably one of the brightest examples of what made early Adam Sandler movies so great: the nonsensical, yet vividly drawn, supporting character. They serve no true purpose and are allotted more screen time than they deserve, but these characters are what ultimately gave the movies so much texture. Happy Gilmore’s chock-full of good lines, but they all fall behind every single one of Hal’s lines in terms of quotability. –Randall Colburn