After a wildly prolific decade of screenwriting and directing that made him the king of teen comedy, John Hughes receded from the cinematic landscape, his legend preserved by the classic 80s trilogy of Sixteen Candles, The Breakfast Club, and Ferris Bueller’s Day Off. Following Hughes’s sudden death, at age 59, last summer, the author delves into his intense connections and sudden breaks with his Brat Pack actors, as well as the essential anomaly of his brief Hollywood reign.

John Hughes never stopped writing. He was notorious for this trait, especially in the 1980s, when he churned out screenplays faster than Hollywood could make them into movies. The script for Sixteen Candles came forth in a two-day burst during the 1983 preparations for The Breakfast Club, so impressing his studio overseers that it jumped the line to become Hughes’s directorial debut, in 1984. By 1987, the year of Planes, Trains & Automobiles, Hughes had already written and directed the “teen trilogy” for which he would be most celebrated—Sixteen Candles, The Breakfast Club, and Ferris Bueller’s Day Off—as well as a lesser teen comedy, Weird Science, and the movie that would actually come after Planes, Trains & Automobiles on the release schedule, the expressly post-teen She’s Having a Baby. Somewhere in this time, he had also managed to write a further two teen pictures, Pretty in Pink and Some Kind of Wonderful, that were off-loaded to another director.

Writing was, for Hughes, not so much a profession as a condition of life. The thoughts that germinated in his brain took a direct path to his hands, which filled notebooks, floppy disks, and hard drives with screenplays, stories, sketches, and jokes. When he wasn’t writing creatively, he was writing about how much writing he was doing. A spiral-bound logbook from 1985 finds Hughes keeping track of his progress on Ferris Bueller. The basic story line, he notes, was developed on February 25. It was successfully pitched the following day. And then he was off: “2-26 Night only 10 pages . . . 2-27 26 pages . . . 2-28 19 pages . . . 3-1 9 pages . . . 3-2 20 pages . . . 3-3 24 pages.” Wham-bam, script done. All in one week.

In recent years, as he withdrew from filmmaking and ceased to maintain any sort of public profile, an air of mystery came to surround Hughes. He had been such a force; what had happened to him? He last directed a movie in 1991—the forgettable Curly Sue—and by the dawn of this century he was no longer sending new screenplays to the studios, though any studio would have been glad to have him.

Yet, in his absence, Hughes’s cultural stock only appreciated. His best movies, the teen trilogy in particular, transcended their origins as light 1980s entertainments to become, first, lodestars for such developing talents as Judd Apatow and Wes Anderson, and then, as these pictures proved their durability on TV broadcasts and DVD, outright classics. It was remarkable enough that a baby-boomer born squarely in the middle of the 20th century had somehow laid claim to the title of Teen Laureate of the 1980s; more remarkable still was that his movies turned out to be a renewable resource, with a reach far beyond the generation for which they were originally intended.

So when Hughes died suddenly of a heart attack while out walking in New York City last August, at only 59 years of age, it wasn’t just the 25th-reunion crowd that fell into mourning and remembrance but nearly the whole of movie-watching America. Duly and fondly recalled were the tragicomic romantic trials of the coltish young Molly Ringwald; the jittery patter of gangly Anthony Michael Hall; the stalking menace and flared nostrils of moody Judd Nelson; and the fictional community that their characters inhabited, Shermer, Illinois, which was at once an Everytown for every teen and an explicit homage to Hughes’s home turf, the North Shore suburbs above Chicago. And again the question arose: What had happened to Hughes—where had he gone, and what had he been up to?

The answer, to some degree, lay in the wisdom of Ferris Bueller, who, as played by Matthew Broderick, delivered the most epigrammatic of Hughes-isms: “Life moves pretty fast. You don’t stop and look around once in a while, you could miss it.”

At some point, Hughes stopped and looked around, and he realized that he didn’t want to make movies anymore. He wanted to be at liberty to spend as much time with his family as he pleased, to work the farm he owned 75 miles northwest of Chicago, and to exult in the resolutely uncoastal ethos of his beloved Midwest. And by 1990, with the release of his highest-grossing movie, the Macaulay Culkin sado-slapstick comedy Home Alone, which Hughes wrote and produced but did not direct, he had the means to put Hollywood and the movies behind him.

For all his success in pictures, Hughes’s directing years turned out to be an aberration in his life—a shortish stretch that required him to do uncharacteristic things like be in L.A. and keep the company of actors. The one normal aspect of this period for him, consistent with the rest of his life, was the compulsive writing. It was a habit that dated back, appropriately enough, to his teen days. “You know that assignment you always get in high school when you’re reading Walden, to keep a journal?” he said in a 1988 interview. “Well, I just kept doing that.”

300 Notebooks
Last autumn, I met with Hughes’s two sons, John III and James, to discuss their father, his movies, and his post-filmmaking afterlife. We convened at a hotel in Lake Forest, Illinois, not far from their parents’ home. The brothers, born in 1976 and 1979, respectively, explained that their mother, Nancy, was still too grief-stricken to join us, though she had given them her blessing to talk. John III is a musician and producer who owns an independent record label in Chicago. He is married and the father of three young children. James, who until recently was based in New York, is a writer and the managing editor of an independent cultural magazine called Stop Smiling. He is married and became a father for the first time last June. It was during Hughes’s second trip to visit his new grandson that he suffered his fatal heart attack. James and his wife are now in the process of relocating to Chicago.

Among the first things John and James showed me was a little red Moleskine pocket notebook, three and a half by five and a half inches in size. Each page within was covered in their father’s neat, extraordinarily tiny handwriting—the cursive equivalent of three-point type. In his later years, Hughes never went anywhere without one of these notebooks on his person, the better to record anything that popped into his head at any time he wished: observations, incidents, editorials, inventories, theories, vignettes, overheard conversations. Sometimes his thoughts erupted into drawings: densely crosshatched caricatures of real-life figures such as Barack Obama and Sonia Sotomayor, or wiggy flights of fancy that variously evoked the styles of Saul Steinberg, Gahan Wilson, and R. Crumb.

“This is extremely representative of what he was like in recent years,” James Hughes said. “Where you have the Smythson of Bond Street attaché case with multiple Moleskines within, and the Pentel fine-art pens he used.”

John and James have found, so far, more than 300 pocket notebooks among their father’s effects (some Moleskines, others Smythsons), and these are but a drop in the bucket of what Hughes left behind: archival papers, old correspondence, personal journals, thick binders containing works in progress, and gigabyte upon gigabyte of computer files.

Going through all this material, said John III, has been “as comforting as it is horribly sad.” The brothers had also discovered a cache of letters that Hughes had prepared for each of his four grandchildren, to be opened and read when they’d reached certain ages. Even James’s little boy, eight weeks old at the time of his grandfather’s death, has a stack of letters awaiting him.

Hughes, his sons say, reveled in grandfatherhood; he relished the concept of growing old and shifting into the role of eccentric paterfamilias. Whereas, in the 80s, he had hewed faithfully to the fashion conventions of the time, collecting expensive basketball shoes and wearing his hair in a rococo power mullet, in his last decade he pointedly dressed in a suit nearly every day, favoring Brooks Brothers and the custom tailor Henry Poole of Savile Row. “I think it bothered him that people his same age, of similar means, were wearing sweat suits and Twittering,” said James. Though he still kept up with new music—Hughes had been a legendarily voracious record buyer in the old days, admired by rock snobs for the acuity of his soundtrack picks—he now viewed it as his primary duty to be, in his younger son’s words, “the curious, engaged grandpa in the seersucker.”

The creative writing he continued to do was, therefore, not necessarily for public consumption. In recent years, he worked in a variety of formats: memoir, short fiction, and, yes, screenplays. But he was content, John III said, to “pump the stuff out for his own satisfaction, comfortable with it never going anywhere.” He’d had his say, and it was time for others to have theirs.

This mind-set was, as contradictory as it may sound, consistent with the one that led Hughes to become the sympathetic voice of teendom in the 1980s. One of his major hobbyhorses—“a constant topic,” in James’s words—was the attention-hogging egotism of his own generation, the baby-boomers. In his view, the boomers did not know when to step aside and cede the stage. “He was kind of upset not to see more people of his generation passing the baton,” John III said. “He wanted to give youth a voice.”

Avatars and Surrogates
Hughes’s own youth has been the subject of much speculation. He was so expert at delineating archetypes—“You see us as a brain, an athlete, a basket case, a princess, and a criminal,” as Anthony Michael Hall’s voice-over letter to the mean principal goes in The Breakfast Club—that viewers have naturally been moved to wonder which type represented the author himself.

In an op-ed piece published in The New York Times six days after Hughes’s death, Molly Ringwald speculated that she and Hall, both of whom appeared in three Hughes-written teen films, were his avatars, “acting out the different parts of his life—improving upon it, perhaps.” Ringwald specialized in playing the sensitive, conflicted, sexually naïve, deeply romantic ingénue who kept posters of alt-rock bands on her walls. Hall was impressively resourceful in playing three distinct iterations of the common geek. So that would have made the teenage Hughes a kind of geek romantic outsider, right?

But then, the DVD commentary for Ferris Bueller’s Day Off features a telling interview from 1986, the year of the film’s release, in which Hughes describes the dynamic among the consummate winner Ferris, his beautiful girlfriend, Sloane (Mia Sara), and Ferris’s sad-sack best friend, Cameron (Alan Ruck), as “this classic third-wheel situation, which I was always in.” You expect Hughes, whose lanky build and soft features weren’t a world away from Ruck’s, to cop to being the third wheel. But what he proceeds to say is “I always had my girlfriend … and some guy in the backseat saying [dopey voice], ‘What’re we doin’?’” Wait! Hughes was the popular kid?

“When you know a little bit about John’s history with Nancy—they met in high school. He was a penguin that mated for life, and so was Ferris,” says Broderick, who, naturally, thinks his character is the most ready stand-in for Hughes.

The truth is that Ringwald, Hall, and Broderick—and Ruck—were all Hughes’s surrogates: refractions and distillations of various parts of a very complex character. Throughout his life, Hughes was at once an old kid and a young fogy. He was a child of the 60s who got married while barely out of his teens; a stolid adman who mischievously and semi-surreptitiously moonlighted as a humor writer; and a homebody midwestern dad who effectively created the Hollywood clique that came to be known as the Brat Pack.

The Holy Grail of Humor
John Hughes spent the first 12 years of his life in the affluent Detroit suburb of Grosse Pointe, Michigan. (He adored the Detroit Red Wings hockey team, in particular its Hall of Fame right wing Gordie Howe, which is why Ruck’s Cameron, a Chicago-area rich kid, incongruously wears a red howe jersey throughout Ferris Bueller.) Though these were the boom years of the American automotive industry, the Hugheses barely clung to middle-class status. Hughes’s father, also named John Hughes, held a variety of salesman jobs to support his wife and four children. The younger John was the second eldest and the only boy.

In 1962 the family moved to Northbrook, Illinois, where Hughes’s father found work selling roofing materials. Again, the Hugheses didn’t fit the wealthy-commuter profile that their town’s name conjured, creating a seam of class anxiety that Hughes would later mine for Pretty in Pink, in which Ringwald’s proletarian character, Andie, struggles with her feelings for a country-club suitor named Blane (Andrew McCarthy).

Hughes turned 17 in 1967, the year that Sgt. Pepper’s Lonely Hearts Club Band came out—perfect boomer timing. He was sufficiently a child of his generation to go Beatles-mad and dress up in imitation of them, pulling together a mod wardrobe that drew quizzical stares in Northbrook. But he was also enough of a romantic and an old-fashioned traditionalist to fall hard that very year for a girl he met while painting homecoming murals: a pretty blonde senior at Glenbrook North High named Nancy Ludwig.

In 1970, when he was 20 and she was 19, John and Nancy did something very counter-countercultural: they got married and settled down. Though Hughes was, at this point, a college dropout, having left the University of Arizona after two years, he was not of the turn-on, tune-in tribe. Rather, he applied himself to scratching out an honest living, juggling jobs at various factories and a printing lab—all the while trying to gain a toehold, somewhere, as a writer. In the early years of his married life, this ambition took the form of his submitting jokes to the big comedians of the time: Rodney Dangerfield, Henny Youngman, Phyllis Diller, Joan Rivers.

In Hughesian fashion, he was relentless, serially pestering the comics with sheaves of gags, neatly typed up on onionskin paper. He tailored his jokes for each comedian’s voice—e.g., for Dangerfield, “I know a guy who’s so kosher he wouldn’t let his son join the ham-radio club,” and for Diller, “My husband thinks my measurements are 34-26-34-hike!” For a nonentity, Hughes did reasonably well as a freelance gagman, making the occasional sale and hearing some of his one-liners get airings on The Tonight Show. But with the going rate somewhere between $5 and $10 a gag, it was no way to make a living.

Yet the joke sheets proved an effective calling card to the advertising world. Hughes used them to hustle his way into an entry-level job at Needham, Harper & Steers, and then, in 1974, a better job at the most prestigious of the Chicago-based ad agencies, Leo Burnett.

At Burnett, he fell under the supervision of Rob Nolan, a creative director who quickly realized he had a wunderkind on his hands. “There was no low level of John that I can remember,” Nolan says. “He was constantly beating away at the typewriter, fueled by coffee and cigarettes.” Hughes flourished, working on dozens of accounts and creating two enduring campaigns: the Edge credit-card test, in which an actor demonstrated the close shave he got from Edge shaving gel by scraping a charge card against his smooth cheek, and the Sugar Corn Pops spots for Kellogg’s that featured Big Yella, a pint-size cartoon cowboy.

Nolan gained such confidence in his charge that he entrusted him with the Virginia Slims account, a plum job that entailed regular trips to the New York City headquarters of the cigarette-maker’s corporate parent, Philip Morris. To Hughes, the main benefit of these trips was that he got the opportunity to hang around the offices of his dream workplace, National Lampoon. He had already managed to get a few humor pieces published in Playboy, but the Lampoon was, in the late 70s, the holy grail for aspiring print humorists. Soon enough, he insinuated himself into its pages, finding a kindred spirit in P. J. O’Rourke, the magazine’s managing editor.

O’Rourke had been toying with the idea of doing an elaborate parody of a Sunday newspaper in a mid-market midwestern city. He had already dreamed up a fictionalized version of his native Toledo called Dacron, Ohio, and the paper was to be called The Dacron Republican-Democrat. “John got it right away,” O’Rourke says, “because John created worlds. He was creative in the most fundamental, Genesis-ian sense of the word.”

The O’Rourke-Hughes collaboration—a convergence of the former’s Dacron and the latter’s nascent imaginary Shermer—yielded 1978’s landmark National Lampoon Sunday Newspaper Parody, which came complete with comics, a magazine supplement, a color ad circular (from a discount store named Swillmart, “Where Quality Is a Slogan”), and fully fleshed-out sections for sports, arts, style, and travel.

Nolan was not oblivious to Hughes’s growing Lampoon workload. The two men hit upon an agreement: Hughes could take mornings to do whatever personal work he wanted, as long as he got his Burnett work done in the afternoon. Still, Hughes felt an ever stronger pull toward the Lampoon, and later admitted to Nolan that he sometimes flew to New York and back on the same day, entirely on Lampoon business, without his overseer’s knowledge—taking care (shades of Ferris Bueller) to leave a full coffee cup on his desk to create the illusion that he’d just stepped out to the bathroom.

In 1979, O’Rourke finally persuaded Hughes to give up his life in advertising. But even the Lampoon, it soon became apparent, was just another way station until the big time beckoned. Hughes never bothered to relocate his family to New York—a place he dismissed, O’Rourke recalls, as “a great city if you cleaned it up and moved everything back 10 feet.” Hughes’s hiring coincided with the moment when the Lampoon was riding high on the surprise success of its first film project, Animal House, and, as O’Rourke says, “everyone suddenly found themselves with an opportunity to pitch a movie. John was the one who took it seriously and had the vocabulary for it.”

Creating “Shermer”
Hughes’s proficiency didn’t translate immediately into screenwriting success. He was a writer on Animal House’s wan, short-lived TV spin-off, Delta House, and saw a variety of projects fall apart. His first writing credit on a feature film was for the Lampoon’s abysmal follow-up to Animal House, a horror-movie spoof called Class Reunion.

Then, unbeknownst to Hughes, Warner Bros. bought the rights to “Vacation ’58,” a short story he had written for the Lampoon in 1979, about a family’s disastrous cross-country drive from Detroit to Disneyland. Matty Simmons, the magazine’s publisher, invited Hughes to adapt his own story for the screen.

Vacation, directed by Harold Ramis and starring Chevy Chase, became one of two breakthrough hits for Hughes in the summer of ’83. The other was the Michael Keaton movie Mr. Mom, his first effort out from under the Lampoon imprimatur. Yet Hughes had not particularly enjoyed these filmmaking experiences. As a control freak who had grown accustomed to micro-managing every aspect of his advertising and print work, he was eager to direct his own scripts—and to exercise his Genesis-ian creativity to the fullest. Enter the populous, teen-infested suburb of Shermer.

Until 1923, the village of Northbrook was known as Shermerville. Hughes’s Shermer was partly Northbrook and partly a composite of all the North Shore’s towns and neighborhoods—and, by extension, all the different milieus that existed in American suburbia. In Hughes’s mind, he would later say, Molly Ringwald’s upper-middle-class character in Sixteen Candles, Samantha, was a passing acquaintance of Matthew Broderick’s Ferris Bueller, while Judd Nelson’s troubled Breakfast Club punk, Bender, came from the same forlorn section of town as Del Griffith, the hard-knock but relentlessly upbeat shower-curtain-ring salesman played by John Candy in Planes, Trains & Automobiles.

As he found his footing as a screenwriter, Hughes dipped into these milieus with an adman’s concision. Each of the teen-trilogy pictures takes place within a short time frame: Sixteen Candles over the course of a weekend; The Breakfast Club and Ferris Bueller’s Day Off over a matter of hours. This wasn’t the narrow focus of a regional indie miniaturist but that of a big-idea guy looking for concentrated impact. “John liked a big canvas,” Broderick says. “He wasn’t going for the slice-of-life approach.”

And Hughes wanted the teen pictures to convey a sort of universal truth: that no age group takes itself more seriously than teenagers. “At that age,” he said, “it feels as good to feel bad as it does to feel good.” Every day has the potential to be the worst day ever, like Samantha’s 16th birthday, or the best, like the day Ferris spends playing hooky.

The first of the Shermer-teen scripts was the least jocular. It was called Detention. For Hughes, it was a mission as much as it was a movie. By dint of having gotten married so young, he and Nancy had spent the early years of their marriage in an unusual circumstance: they were closer in age to their teen neighbors than to the homeowning parents of those teens. “I saw how their lives at 14 and 15 were different than mine had been,” Hughes said in one of his last long interviews, for Sean M. Smith’s authoritative oral history of The Breakfast Club, in the December 1999 issue of Premiere. “My generation had sucked up so much attention,” Hughes said, “and here were these kids struggling for an identity. They were forgotten.”

In 1982, before Vacation and Mr. Mom had lent him any Hollywood clout, Hughes made a small-time deal with A&M Films to direct his Detention script, which concerned five kids from five different social groups who are confined to the library of Shermer High for a single Saturday. (The project took on the title The Breakfast Club after Hughes picked up the phrase from a friend’s teenage son. “It actually referred to morning Detention, not Saturday Detention, but I figured no one would call me on it,” he said.) The budget was $1 million, minuscule even in those days. But Hughes soon became “antsy,” he recalled, about debuting with a potentially uncommercial chamber piece whose failure could spell career doom. So he set to work on a more lighthearted story about a Shermer girl whose family, in the fevered run-up to her older sister’s wedding, forgets all about her 16th birthday.

Sixteen Candles was promptly optioned in 1983 by Ned Tanen, the former president of Universal Pictures, who had just left the studio to set up an independent company, Channel Productions. In his tenure at Universal, Tanen had shepherded several youth-oriented movies into existence, among them American Graffiti, Animal House, and, just the year before, Fast Times at Ridgemont High, the work of a first-time screenwriter (Cameron Crowe) and a first-time director (Amy Heckerling). He was willing to take a similar chance on Hughes, and agreed to adopt The Breakfast Club project as well—provided Hughes made Sixteen Candles first.

Molly as Muse
As the story goes, commercial considerations weren’t the only impetus for Hughes’s writing Sixteen Candles. While leafing through headshots in search of potential Breakfast Club cast members, he froze upon the glossy of a pale-skinned young actress with red hair and puffy, tired eyes—pretty, but not conventionally so.

“From what I heard from him,” says Ringwald, “he put my headshot on the bulletin board by his desk and wrote Sixteen Candles over a weekend. And when it came time to cast it, he said, ‘I want to meet her: that girl.’”

Ringwald, 15 years old in 1983, had just appeared in Tempest, Paul Mazursky’s modern-dress re-write of William Shakespeare’s final play. Compared with the old pro Mazursky, the 33-year-old Hughes was from another planet: youthful and spiky-haired, with an unlined face, circular-lens eyeglasses, and the latest in fresh Nike high-tops—“Not what I really thought of as a film director,” Ringwald says. But she left her first meeting with Hughes excited. There was no audition. Ringwald and Hughes simply talked—Hughes confirming his hunch that she was the right girl to play Samantha, Ringwald bowled over by his interest and believing it Kismet that they shared a birthday, February 18. “I feel like we sort of mutually idealized each other from the get-go,” she says.

Sixteen Candles is constructed as a love triangle of sorts, with Samantha, a sophomore, pining for a handsome, remote senior named Jake, while a pesky freshman—known alternately as the Geek or Farmer Ted—indefatigably pursues her. For Jake, Hughes cast a chiseled Bruce Weber model named Michael Schoeffling, whose dreamy looks and shy demeanor were just right for the character, a rich jock too kind and sensitive to fulfill his socially prescribed duty to be an arrogant misogynist. For the Geek, Hughes remembered the child actor who had played the Chevy Chase character’s son in Vacation, Anthony Michael Hall: a little blond Puck with inborn comic timing.

Hall, like Ringwald, turned 15 the year Sixteen Candles was made, though he was still downright fetal in appearance: wavy hair and big eyes atop a head and body that were waiting in vain to fill out. The big joke of the Geek character is that his physical immaturity and obvious sexual inexperience don’t prevent him from playing the suave lover man and brash ringleader of a passel of nerd underclassmen—“the king of the dipshits,” as he confesses to Samantha when they finally lower their guards and have a heart-to-heart in the auto shop of Shermer High while a dance goes on in the gym. (The movie was shot in and around Skokie, Illinois, with the school scenes filmed in a defunct high school, Niles East.)

The auto-shop scene has come to be celebrated for its heart and authenticity, and Ringwald and Hall sensed its specialness even as they filmed it, not least for the way Hughes trusted them to add their own flourishes—for example, Ringwald’s suggestion that the Geek apologize for having been such a “poozer” on the bus (a word she appropriated from Dr. Seuss’s I Had Trouble in Getting to Solla Sollew), and the desperate body language Hall brought to the Geek’s last-ditch attempts to make out with Samantha, swinging his whole right leg around her spasmodically, as if trying to experience as much surface area of real girl as possible.

“It was evident to me soon after meeting John that he was very collaborative,” says Hall, who, at 41, finally has filled out. (He now looks like Steve McQueen circa Bullitt.) “He obviously had a knack for dialogue, but he was never precious or uptight about me changing anything. It was so empowering: here I was, a 15-year-old still in puberty!”

Sixteen Candles was not without its broad, farcical crudities and nods to Hughes’s baser Lampoon-ish instincts: a gratuitous boob scene, a bunch of characters presented as tissue-thin grotesques (Samantha’s four querulous grandparents, her sister’s mafiosi future in-laws), and the vaudevillian-throwback character Long Duk Dong, who was putatively a Chinese exchange student but was played by a Japanese-American actor (Gedde Watanabe), assigned a line of Japanese dialogue (“Banzai!”), and given a vaguely Vietnamese, vaguely phallic name that, every time it was uttered, was accompanied by the sounding of (oh, dear) a gong.

But Hughes’s work with Ringwald and Hall transcended all that. Pauline Kael, The New Yorker’s tough-cookie film writer, devoted a lot of space to Sixteen Candles and its juvenile stars in her May 28, 1984, “Current Cinema” column, commending the movie for being “less raucous in tone than most of the recent teen pictures; it’s closer to the gentle English comedies of the forties and fifties.” She was enchanted by Ringwald’s “offbeat candor,” and relished Hall’s leering attempt to smile sexily through braces (“pure weirdness”) and the way the actor “moves like Steve Martin, and even more confidently.”

The movie’s box-office performance fell short of Universal’s expectations. But Hughes had forged a tight bond with Ringwald and Hall, both of whom were carried over into his next project, The Breakfast Club. This meant more time on location in the Chicago area; the library that served as the movie’s primary location was actually a set constructed inside the gymnasium of yet another abandoned suburban high school, Maine North, in Des Plaines. Ringwald and Hall would be joined by three other young actors, Emilio Estevez, Ally Sheedy, and Judd Nelson. But, says Ringwald, she and Hall “were sort of viewed as the teacher’s pets. John would take us to concerts and invite us to his house.”

Ringwald, at 16, now found herself playing the heady role of artist’s muse. She and Hughes fell into marathon bull sessions about life, their feelings, and, especially, music. Hughes introduced Ringwald to Chicago blues—taking her to hear Koko Taylor and Junior Wells sing at Kingston Mines, the North Side blues club—and educated her in the ways of his beloved Beatles. Ringwald, for her part, found common ground with Hughes in their shared taste for British-import pop. A California girl, she gushed to Hughes about the postpunk and New Wave music that she heard on KROQ, the Anglophilic L.A. station to which she was devoted. Pretty in Pink, she says, was written for her after she played Hughes the Psychedelic Furs song of that title.

Hall’s relationship with Hughes was less intense than Ringwald’s but more familial. The Hugheses had by then bought a large two-story Colonial in the village of Northfield, Northbrook’s smaller, posher neighbor. Hall, a child of divorce, slept over at the Hugheses’ on weekends and reveled in the warmth and nuclear-family normalcy of the home that John and Nancy had created. “I became their third son, in a way,” he says.

“Seemed Like One of Us”
Hughes gave his young Breakfast Club stars plenty of latitude to improvise with the cameras running. It was only a 32-day shoot, but he shot more than a million feet of film: par for the course for Martin Scorsese, but unheard of for a low-budget teen picture.

The teen-trilogy actors note that, unlike any other adult they knew, Hughes had ready and vivid access to his own adolescence and the feelings it engendered. His son John attributes this to “an insane memory that could really call back on that stuff,” but Hall wonders if, in fact, these childhood feelings were just barely latent—“whether John never grew up on the inside, on some level.”

For Ringwald, the sheer bliss of working with a director who “seemed like one of us” was sometimes offset by the discomfort of enduring Hughes’s very teen-like sulks. “He was so easily slighted and hurt,” she says. “He would always go to the place that somebody didn’t care about him.” She recalls a mortifying episode in which she extended a trip home to Los Angeles by one day to visit her gynecologist. At her age, she was too embarrassed to tell Hughes the reason for her extra day out West, “and John was sure that I was meeting with someone for another movie. He flipped out. He thought that I was not committed to him. And this was somebody who adored me. It was really terrifying.”

“You had to be careful with him,” says Broderick. “I remember him taking me to one location, the Art Institute, and him saying, ‘This is where you and Mia kiss.’ And I had not been reading the stage directions carefully, and I was like, ‘Oh, we kiss at the museum?’—something I thought was pretty innocent. But to him it meant that I was not prepared, and he took that as a personal affront, that I didn’t care about him: ‘O.K., so we won’t be friends. We’ll just do our work.’ But he also had the ability, by that evening, to take you to dinner with a bunch of people and tell you what a genius you were.”

rior to The Breakfast Club’s release, the executives at Universal were convinced they had a dud on their hands. But Hughes was the one whose instincts proved correct: the movie was an immediate hit in the winter of 1985.

As hoary as it sounds, The Breakfast Club spoke to a generation. The elements that grown-ups perceived as ponderous and risible were precisely what made the movie so real to teens: Nelson’s hoodlum, Bender, working himself into a paroxysmal lather while re-enacting a fight in his broken home (“Fuck you!” “No, Dad, what about you?!”); Sheedy’s loner goth-freak, Allison, emitting awkward squeaks and rustling dandruff from her hair to decorate a winter snowscape she was doodling; Estevez’s champion wrestler, Andrew, coming undone from his military bearing as he admits to hating his bullying father; Ringwald’s privileged priss, Claire, confessing her virginity under duress; and Hall’s fragile, scared math whiz, Brian, breaking down in tears as he confronts the high expectations placed upon him by his parents.

The Breakfast Club’s success had the further effect of casting Sixteen Candles in a new light, as Chapter One in the continuing oeuvre of the teen auteur John Hughes and his comely muse, Molly Ringwald. The following year, when Pretty in Pink came out, Ringwald landed on the cover of Time magazine.

“Hughes is 36, but he provides no adult’s-eye view of teen problems,” the accompanying article said. “Instead, he gets spookily in sync with the swooning narcissism of adolescence: that teachers are torturers, that parents are sweet but don’t quite understand, that friends and lovers are two distinct species. . . .”

Tucked away in the Time story, though, was an intriguing, unexplicated quotation from Ringwald. “I don’t really see him anymore,” she said of Hughes. “I still respect him a lot, and if he gave me a good script, I’d read it. But I don’t think we’ll work together again real soon.”

In fact, they didn’t work together ever again. The story behind Ringwald’s words, she says, is that she and Hughes had by then fallen out—or, at any rate, he had fallen out with her. Near the end of the filming of The Breakfast Club, she and Hall began dating. Both 16, they were by far the youngest cast members; Nelson, Estevez, and Sheedy were in their 20s. It wasn’t a shocker that two teenagers working together on two consecutive films would hook up, but, in Ringwald’s perception, their little romance upset Hughes. “He did not like it at all,” she says. She still doesn’t fully grasp why this was—perhaps because she and Hall had veered off script from the ordained narratives of their creator, creating a story line of their own?

Publicly, Hughes remained gracious, speaking complimentarily of her in the Time piece. But Ringwald was surprised when he deputized his protégé, Howard Deutch, to direct her in Pretty in Pink. And though Hughes spent time on that film’s set as its writer and executive producer, he rarely spoke to her. “It was very hurtful,” she says, “and it still hurts. I cared very, very deeply for him, and he had a huge impact on my life—not just in terms of my career but my development as a person, as a woman.”

Hall recalls no cross words with Hughes, about Ringwald or any other subject. Immediately after The Breakfast Club, he and Hughes happily made another film together, Weird Science—“a dopey-assed comedy,” in its creator’s estimation, but yet another chapter in what looked to be an enduring, fruitful collaboration. No less an authority than Stanley Kubrick compared the Hall-Hughes partnership to that of Jimmy Stewart and Frank Capra. (Indeed, Hall was offered the lead part in Kubrick’s Full Metal Jacket before Matthew Modine, but withdrew from consideration after protracted negotiations between his camp and the director’s bogged down.)

But Hall, too, saw his relationship with Hughes come to an abrupt and puzzling end, at least in his eyes. It’s his belief that both the Duckie part in Pretty in Pink and the title part of Ferris Bueller’s Day Off were conceived with him in mind. He suspects that he, like Ringwald, inadvertently poisoned the well with Hughes by expressing a desire to work with other filmmakers. After Weird Science, Hall simply couldn’t get Hughes on the phone anymore.

Around 15 years ago, Ringwald sought to reach out and smooth things over with Hughes. Living in Paris, she had been on a François Truffaut video kick, watching the series of films that the French director had made with the actor Jean-Pierre Léaud. Recognizing something of herself and Hughes in the Léaud-Truffaut collaboration, she was inspired to send Hughes a note saying how much he meant to her. A week later, she took delivery of an enormous bouquet of flowers: Hughes’s final communication to his former muse.

Escape from L.A.
By the time of Ferris Bueller’s Day Off (1986), in which his three truant protagonists gallivant merrily through Chicago, checking out Wrigley Field, the Sears Tower, the Art Institute, and a German-American parade going down Dearborn Street, Hughes was living in the Brentwood section of Los Angeles. The movie might as well have been called John Hughes’s Homesickness Reverie.

Hughes had moved his family out West in 1984, when Universal insisted that he edit The Breakfast Club in L.A. Earlier that same year, before the studio’s edict, Hughes vented to Roger Ebert of the Chicago Sun-Times that its competitor, the Chicago Tribune, had referred to him, mistakenly, as a “former Chicagoan.”

“As if, to do anything, I had to leave Chicago,” Hughes said. “I never left. I worked until I was 29 at the Leo Burnett advertising agency, and then I quit to do this. This is a working city, where people go to their jobs and raise their kids and live their lives. In Hollywood, I’d be hanging around with a lot of people who don’t have to pay when they go to the movies.”

The California stay was supposed to be temporary, but one year turned into two, and then, ultimately, into four and a half. John and Nancy kept the house in Northfield so that the boys could enjoy a proper Christmas with snow and chill in the air—and, not so subconsciously, so that a ready escape hatch to sanity existed.

Hughes simply never took to L.A. His sojourn there, though it coincided with what was arguably his artistic peak, sowed the seeds for his post-filmmaking life. It made him realize what he did and didn’t value. He had no capacity or tolerance for industry schmoozing, no interest in keeping up with his young actors’ emerging Brat Pack party circuit. What did matter to him was his family.

Especially in his L.A. days, his sons say, their father got all the adult companionship he required from his film crews and the editors he worked with in postproduction, and otherwise maintained few close friendships. “I think he looked at family as a sort of wall,” John III says. “It gave him a sort of protection for not getting drawn out of the house. We were his social activity.” The Hughes home itself was a bustling, happy place, with an open-door policy for the boys’ friends and the actors Hughes liked—Broderick remembers dropping by often to use the pool—but beyond its warm confines, Hughes actively resisted being social.

One notable exception was the actor with whom he worked most regularly as he transitioned out of teen pictures: the reliably brilliant SCTV stalwart John Candy, the star of Planes, Trains & Automobiles (1987), The Great Outdoors (1988), and Uncle Buck (1989). Candy, though he was from Toronto rather than Chicago, led a life similar to Hughes’s: big hockey fan, big family man, strong marriage, two young kids.

“Our families basically merged,” says Candy’s daughter, Jennifer. The Candys kept a farm in Queensville, Ontario, an hour north of Toronto, and regularly welcomed the Hugheses as guests. “A gentleman’s farm, a hundred-odd acres,” Jennifer says. “From that, John Hughes got the idea to have his farm, and he took it to the next level.”

In 1989, Hughes purchased the first parcel of what he would call Redwing Farms, in western Illinois near the Wisconsin border. It has grown to be more than a thousand acres in size. The farm allowed Hughes to exercise his Genesis-ian creativity in the most literal, biblical sense. Much of the land, when he acquired it, was barren. Hughes embarked on an ambitious plan to reforest it with indigenous trees and other plantings, undertaking thorough botanical and dendrological research to learn what the property would have been like pre-cultivation. With a team of landscapers and farmers, he also set up a section of the property as a refuge and working farmstead, growing crops, raising Devon cattle, and designing and planting elaborate hedgerows, the subject of much notebooking in his later years. It was his last big production.

There was no single triggering incident that compelled Hughes to pack it in as a filmmaker; the withdrawal was gradual. At the end of the 1980s, he gave up the Brentwood house and relocated to the Midwest for good, acquiring a new home in Lake Forest and setting up his company, Hughes Entertainment, on the former campus of New Trier West High School, in Northfield. He stopped directing after Curly Sue, limiting himself to screenwriting and producing, mostly on slick but superficial family entertainments, such as the cutesy dog movie Beethoven (1992) and the 1990s remakes of Miracle on 34th Street and 101 Dalmatians.

Hughes was shaken by John Candy’s sudden death, of a heart attack, in 1994. “He talked a lot about how much he loved Candy—if Candy had lived longer, I think John would have made more films as a director,” says the actor Vince Vaughn, a fellow Lake Forester and one of the few show-business people with whom Hughes was friends in recent years.

By the 2000s, his days as even a screenwriter were done. His compulsive writing remained constant, but it was directed away from movies and toward himself—and, sometimes, his family. “He was a relative latecomer to e-mail,” says James. “But I remember that, when he did get it, we were all like, ‘Oh, shit—here it comes.’” Hughes’s e-mails were thought avalanches, lavish interdisciplinary discourses on current events, political scandals, the Chicago Black Hawks, movies he’d watched on TCM, authors he’d seen on C-span’s Booknotes, the trees he was planting, the obscure hillbilly music he’d taken to compiling, and whatever else happened to be on his mind. “In his later years it was sort of his primary job, to ingest all this material and riff on it,” says James.

It wasn’t just e-mails either, but gab. “I’d go to his house at seven at night and not leave until seven the next morning,” says Vaughn. “We’d be literally engaged in conversation for 12 hours. About anything, but especially music. His knowledge of music was incredible.”

Indeed, apart from farming, music was Hughes’s most consuming passion. It pained him that he was so identified with the 80s alterna-pop of his teen films, since that music represented but a thimbleful of the many genres and idioms he enjoyed. His iTunes library filled several hard drives, and he planned the playlists for his sons’ weddings as carefully as he had the soundtracks for his movies. In recent years, he took to dispensing pre-loaded iPods to people he liked, much as he’d assiduously compiled mix tapes for Ringwald and Broderick in the old days. The last time he ever saw Hughes, in November 2008, Chris Candy, John Candy’s 25-year-old son, was the recipient of such an iPod, “an incredibly eclectic four-gig, thousand-song mix tape, basically,” Candy says. “I have a local radio show on a college station in L.A., and when John passed away, I just put that iPod on ‘shuffle’ and let it play as my tribute to him.” It was this iPod, returned on loan, that the Hughes family used as background music for Hughes’s funeral.

Last Picture
The evening of Wednesday, August 5, 2009, was a happy one for Hughes. He and Nancy had arrived in New York from Chicago in time to drop in on James and his wife, have dinner, and take lots of photographs and video of their new grandson. Hughes was conversationally “on fire” that night, James says, “in the best possible mood.” After dinner, parents bade good-bye to son and daughter-in-law with plans to meet again the next day.

The morning of August 6, Nancy awoke in her Manhattan hotel room to find her husband’s side of the bed empty, which was not unusual. It was Hughes’s custom to get up early and enjoy a morning constitutional when staying in New York. The routine provided him with an opportunity to get a head start on his relentless observing, sketching, and note-taking.

James was eagerly awaiting the chance to talk with his father about the death of the great screenwriter Budd Schulberg, whose obituary was in the papers that morning. Both Hugheses were fans of A Face in the Crowd, the connoisseur’s choice over Schulberg’s more celebrated On the Waterfront, and surely, James thought, a compelling John Hughes riff on the life and oeuvre of Schulberg was forthcoming.

But then the terrible news reached James, as it had already reached Nancy, and would soon reach John III back in Illinois: Hughes had collapsed on a sidewalk a few blocks from the hotel. He was rushed to Roosevelt Hospital, near Lincoln Center, and pronounced dead of a heart attack.

His death was completely unexpected. Though he had been a chain-smoker for most of his adult life (Tareytons in his adman days, low-tar Carltons thereafter), he had finally kicked the habit in 2001. He had displayed no recent signs of ill health.

“I lost two people with his death,” John III says. “I lost my father, which comes with its own territory. But, really, that was second to losing him as a friend, collaborator, and mentor to my children.”

Says James, “You almost wanted to pick up the phone to talk about John Hughes’s dying with him.”

The notebook that Hughes was carrying with him when he died, a red Smythson Panama, contained no new entry for August 6, though August 5 was filled with a detailed description of the hotel—as if setting the scene in a screenplay—and warm notes about his visit with his grandson. The family also recovered the camera that Hughes had been carrying on his last walk. It contained a few photographs he’d taken that very morning: neatly composed streetscapes. “It’s some small comfort to us that we know from the spot where the ambulance arrived, and from where his last picture was taken, that it was a small distance—that it was sudden,” James says.

More comforting still, James says, is that, “when he passed away, he was doing something he loved. He was out note-taking and observing”—even if the notes were mental and photographic rather than pen-to-paper. The point is: John Hughes never stopped writing until his heart stopped beating.

David Kamp is a Vanity Fair contributing editor.