Movie

The funniest movies tend to burrow into our brains like no other form of popular entertainment. Through repeated viewings and earworm quotes, they create unconscious templates for life’s milestones and stopovers — dating, road trips, the college experience, marriage, the working world — and remind us of moments in time as well as entire eras. They’re comfort food and therapy, high art and cultural critique, nestled lovingly amid fart jokes and crotch punches.

The best comedy movies also enjoy a freedom that seems out of place in most other media, with run-times that allow them to develop complicated but self-contained worlds, the full buffet of acting, editing, and musical options, and the (frequent) R ratings that give them the appropriate range of artistic motion. “Comedy is subjective, ” we’re constantly told. Maybe, but if something stays funny for decades it’s clearly reaching across cultures and contexts to tweak our collective nipples for a reason.

Here are our picks for the best of the best.

20. Office Space (1999)

Before Office Space, most people knew about Mike Judge’s crass but perceptive work via Beavis and Butthead, which only hinted at the multi-textured (if equally dude-centric) worldview of Office Space. Fortunately, most people can instantly relate to this terrifyingly beige universe in which TPS reports, mind-numbing repetition, and TGI Friday’s-style team spirit become the occasion for quietly absurdist field notes on corporate servitude. Select jokes, like David Herman (a.k.a. Michael Bolton) turning down his Scarface song when a black guy strolls past his car, turn lazy cultural role-playing into cutting social commentary. Most have become part of the lexicon. All have aged shockingly well.

19. Clueless (1995)

Often dismissed as a candy-coated time capsule of ’90s teen culture, Clueless is (as any true fan knows) a classic comedy of manners and social critique inspired by Jane Austen’s Emma. Let Heathers have the psyche-scarring and in-fighting; Clueless takes awkward, hormonal, status-obsessed interactions to sublime levels through heightened dialogue and a startling clarity of ideas. Many of the best comedies want to make sure you’ve seen their dark underbellies, but as Mean Girls and others have proven, laugh-out-loud films aren’t required to vibrate on a frequency of cartoon violence and subtle (or not) misogyny to make their marks.