National Lampoon's Vacation (1983)
While Hughes' first screenwriting assignment for the National Lampoon team (Class Reunion) didn't exactly earn him many plaudits, his second film for the comedy publication helped launch his career properly.
Vacation has its origins in the short story that got his foot in the door of the Lampoon mag - a tale based on a real family trip back in the 1950s.
Harold Ramis brought the movie to life and it provided the perfect vehicle (pun entirely intended) for Chevy Chase to indulge himself as the increasingly frustrated Griswold family attempts to drive to Wally World.
Wacky yet warm and witty to boot, Vacation still stands as a classic comedy.
Sixteen Candles (1984)
Talk about making a splash with your first film.
Hughes' initial turn in the director's chair proved that his writing skills weren't the only talent he possessed.
It's an intimate, artful and funny tale of a girl (Molly Ringwald) put through the emotional ringer around her 16th birthday.
Many of the teen staples were established here - awkward, pining friend; nervous, sexually eager but unsure heroine; smooth jock.
But while Hughes created the stereotypes, he also breathed life into them, making for a brilliantly observed job by a first-time director.
The Breakfast Club (1985)
How do you follow Sixteen Candles? You take the teen drama up another notch and carefully create another instant classic.
Five different high schoolers meet in detention, and between them, they learn that they're not as unique as they all thought.
It's far too basic a synopsis for a beautifully written and directed film that explores youth, yearning and heartbreak, with plenty of opportunity for rebellion.
It's most film fans' favourite teen flick, and for good reason. Its emotional impact is as varied as its characters. It's moving, funny, intelligent, dark, weird and original.
It provided the voice for a generation and changed the teen template forever. Before, the teachers were the central figures of the high school flick. Forever after, it would the kids that would provide the main focus.
Weird Science (1985)
Switching gears, Hughes opted for more of a romp, though the story of two geeks (Anthony Michael Hall and Ilan Mitchell-Smith), tired of being shunned by their peers, decide to have a stab at creating the perfect woman.
Thanks to a combination of '80s style high technology and a fortuitous lightning strike, the pair get more than they bargain for with Kelly LeBrock's sensuous Lisa.
It's a genius concept, but Hughes refuses to play it just for cheap laughs, layering in a warning about being careful what you wish for...
Even in a puerile sex comedy John couldn't help providing a deeper meaning.
Pretty In Pink (1986)
Often credited solely to Hughes, Pretty In Pink was actually directed by Howard Deutch, who deserves some of the credit for this truthful, searching film.
Hughes was the writer, and while the story is an old one (lovers from different groups trying to be together), Hughes gives it enough of a fresh spin to make it work.
And it's a good opportunity to talk about one of Hughes other key gifts - his soundtrack skills.
Whether he was watching the recent music scene (he named the film after The Psychedelic Furs' 1981 new wave single Pretty In Pink) or giving classic songs fresh life (we can't hear Try A Little Tenderness without seeing Duckie dance) Hughes' ear for music added genuine depth to his films. It's a major part of what makes his movies so memorable.
He may not have been the sole creator of Pink, but we're pretty sure he was in charge of the music, if his past and future film scores are to be believed...
Ferris Bueller's Day Off (1986)
Who hasn't, on a boring day at school, fantasised about skipping out, grabbing friends and going on an adventure?
With Ferris Bueller, Hughes took that dream and span it out, sending Matthew Broderick's endlessly charming hero on one crazy day around Chicago.
It made an early star of Broderick, but there's fun to be had too with Alan Ruck's uptight, nervy best pal Cameron and Mia Sara's encouraging girlfriend Sloane.
It's another update of an original template, with Ferris talking to the camera with as much cheeky charm as Michael Caine's Alfie; but Hughes gives it so much manic energy if feels like something you've never seen before or since.
It's got several soundtrack set-pieces, it's got heart, wit and endless invention, unforgettable characters, a near-constant sense of rebellion... When people ask us what the ultimate Hughes movie is, we normally reply...
Bueller?... Bueller?...Bueller? Anyone? Anyone?
Some Kind Of Wonderful (1987)
While Hughes once again handed over the directing reigns to collaborator Howard Deutch, his fingerprints are all over this tale of a tomboy (Mary Stuart Masterson) who discovers she's in love with best mate Keith (Eric Stoltz).
The characters feel and act like real people and unlike many unrequited crush films, and the journey is more important than getting to the moment when the pair get together.
One of Hughes' most underrated flicks. It might not bounce of the walls like Ferris and his mates, but it's got as much genuine heart as anything in Hughes' back catalogue.
Planes, Trains And Automobiles (1987)
The writer/director made a seemless transition from teen stories to grown-up issues with this farce of frustration.
Screwball comedies are rarely concerned with the heart (beyond some odes to lovesick nonsense), but that's not the way Hughes works - he turns the central pair, played by Steve Martin and John Candy, into believable people who share an aim to get home for Thanksgiving.
The journey is once again the important part, though this time it a comedy of errors that has them thrown together even though it's clear they don't get along.
There's also a sweetness at the film's core that has you cheering for the pair even as their situation gets worse.
But, more than anything else, Planes, Trains And Automobiles is absolutely hilarious. All together now...
THOSE AREN'T PILLOWS!
The Great Outdoors (1988)
With Howard Deutch once more at the helm, Hughes reunited with John Candy, and this time paired him with Dan Aykroyd in another tale of mismatched types clashed together.
Candy is Chet Ripley, who just wants to enjoy a family trip in the woods. But his hopes are shattered when his annoying, snooty brother-in-law (Aykroyd) and his equally snobby family show up.
While it doesn't quite capture the anarchic energy of Planes, it's still a solid comedy with plenty to recommend it.
Home Alone (1990)
Hughes began to step back more from filmmaking in the early '90s, but he proved that he still had the ability to write winners.
It might not have been an award-grabber, but if Oscar gave out gongs for anarchic, wish-fulfillment fun, it would have swept the board.
With Hughes' script providing the template, Chris Columbus orchestrated the madness as Kevin McCallister (Macaulay Culkin, in an iconic early role) fights off scheming, stupid burglars.
It allowed Hughes to be the voice of a new generation. Even if that voice did only say things like "ARGH!" after slapping on a bit of aftershave.
It's a chaotic classic, with a brilliant sequel to boot.