Hughes wrote, directed, or produced some of the most beloved and influential films of the 1980s, from National Lampoon's Vacation through Planes, Trains, & Automobiles. He revolutionized family friendly live-action comedies in the 1990s. And despite his reputation as a retired recluse, he was credited under a pseudonym for work on both Maid in Manhattan and Drillbit Taylor in the 2000s.
But (the huge influence of Home Alone on a slightly younger generation aside) he'll obviously be best remembered, forever, for his still-beloved high school comedies. They were, and are, remarkable for a few reasons: strong female leads or supporting characters, a focus on a slightly idealized and exaggerated reality instead of peeking-in-the-girls-locker-room outrageousness, and, as we mentioned, class.
His movies dealt seriously, if not always realistically or positively, with class as experienced by, not coincidentally, public school teenagers growing up in the North Shore suburbs of Chicago. His rich suburban kids are neglected by parents more concerned with material goods than their children's well-being and his poor suburban kids are often just flat-out neglected or abused.
Hughes was raised in the Chicago suburbs, where he developed his loathing for (and, frankly, fixation on) the entitled trust fund kids."I knew kids that in the third grade would say, 'When I'm 18, I'm getting $22 million dollars.'" This never translated into political liberalism for Hughes (he shared that weird '80s pretend-counterculture conservatism with a lot of his talented comedian colleagues), but the consciousness of having not-so-much and being forced into dealing with those fascinating creatures who have too much underpins all his crucial '80s work.
So. Yes. Sixteen Candles, Pretty in Pink, the gender-flipped (and superior) Some Kind of Wonderful, the still-hilarious Ferris Beuller's Day Off and The Breakfast Club—that's a pretty good legacy, and they're so ingrained in the popular culture that it's hardly worth it to exalt each one in detail.
The entirety of Pretty in Pink is available on YouTube, for now. The opening Ferris Bueller monologue remains a comic masterpiece.
Hughes began his career as a copywriter, sold jokes to Rodney Dangerfield, and eventually joined the National Lampoon staff. Despite his incredibly influence and obvious status as an auteur, he directed only eight films, from 1984 through 1991.