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‘Pretty in Pink’ at 30: The Best and Worst Films of John Hughes

Before movies like “Say Anything” and “Perks of Being a Wallflower,” and TV shows like “Dawson’s Creek” and “My So Called Life,” John Hughes’ classic high school romance “Pretty in Pink” dared to depict teenage love with a poignancy and truthfulness that felt both natural and wildly sentimental. Released on February 28, 1986, it remains one of Hughes’ most beloved movies. On the 30th anniversary of “Pretty in Pink,” here’s a look back at John Hughes’ 10 finest films, plus five that didn’t quite make the grade.

The Best…

10) Uncle Buck (1989)

John Candy played the title role of a lovable oaf whose babysitting skills are put to the test in this lightweight yet undeniably funny family comedy. The fifth of eight Hughes films in which he appeared, Candy showed winning chemistry with 9-year old Macaulay Culkin in what remains a career highlight. Though a 1990 “Uncle Buck” sitcom starring Kevin Meaney was cancelled after one season, a new television series is currently being developed.

9) Some Kind of Wonderful (1987)

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Hughes wrote this thoughtful romantic drama about a working class high school student whose crush on a wealthy, popular girl prevents him from recognizing his true soulmate waiting nearby with drumsticks in hand. Once again capturing the unique vernacular of the average American teenager, the film’s script contains a beautifully written scene in which Eric Stoltz’s melancholic young grease-monkey admits to his father that he’s one of those guys that just don’t fit in.

8) Weird Science (1985)

This sci-fi comedy about two geeks who create their very own dream girl during a lightning storm shows Hughes at his most outrageous. As the teenage Dr. Frankensteins, Anthony Michael Hall and Ilan Mitchell-Smith ground the dumb-yet-smart concept with genuine character and heart. Meanwhile, co-star Kelly LeBrock gives their supernatural sexpot a no-nonsense personality to be reckoned with. But it’s Bill Paxton who steals the show as the world’s worst older brother.

7) Christmas Vacation (1989)

The third film in the National Lampoon series, this hilarious holiday comedy finds the beloved Griswold family struggling to keep the joy of Christmas alive while obnoxious neighbors, disgusting relatives and rampaging squirrels make their home a living hell. Based on his short story “Christmas ’59,” which appeared in the Lampoon magazine nine years earlier, Hughes’ big-hearted script is a classic farce filled with one laugh-out-loud gag after another.

6) Pretty in Pink (1986)

The Psychedelic Furs lent Hughes inspiration for this sweet story about a girl from the wrong side of the tracks who falls hard for a local rich kid. Directed by three-time collaborator Howard Deutch and starring frequent muse Molly Ringwald, Hughes’ screenplay is one of his most unabashedly romantic. Featuring memorable turns by Jon Cryer, Annie Potts and James Spader, along with an era-defining soundtrack, “Pretty in Pink” makes sentimentality seem fresh.

5) National Lampoon’s Vacation (1983)

Hughes joined the staff of the National Lampoon magazine after penning a short story titled “Vacation ’58,” which was based on his real-life travel experiences. Eventually, he expanded the piece into the screenplay for this Chevy Chase classic. Co-starring Anthony Michael Hall, who worked with Hughes on his next three features, this tale of a hapless everyman who packs his wife and kids into the Family Truckster is one of the most quotable comedies of the ’80s.

4) Sixteen Candles (1984)

At a time when most movies portrayed high school students as nothing more than sex-starved idiots looking to cause havoc, Hughes’ directorial debut bucked the trend. A perceptive coming-of-age comedy about a day in the life of one hopelessly stressed teenage girl, “Sixteen Candles” found humanity and decency in even its weirdest characters. In her breakout role, Molly Ringwald is radiant playing a teen whose birthday is one embarrassment after another.

3) Ferris Bueller’s Day Off (1986)

Hughes had Matthew Broderick in mind when he conceived the irrepressible title character of this stylish high school comedy. Playing the best friend everyone wishes they had, Broderick delivers many of Hughes’ funniest lines directly into the camera. The actor’s winking charisma charmed first lady Barbara Bush enough that she quoted his “Life moves pretty fast” mantra during a commencement address at Wellesley College.

2) Planes, Trains & Automobiles (1987)

Having written and directed four films in a row about teenagers, Hughes broke new ground with this critically acclaimed comedy about two mismatched travelers forced to rely on each other as they make their way home for Thanksgiving. The chemistry between Steve Martin and John Candy is magic in a story that delivers big laughs and big heart in equal measure. A delightful mix of sight gags and keenly observed character moments, “Planes, Trains & Automobiles” is one of the funniest road movies ever made.

1) The Breakfast Club (1985)

Though he’d written several box office hits and directed one comedy prior to “The Breakfast Club,” Hughes shot the movie in a single location to minimize budgetary risks. And yet it’s that intimate, pressure-cooker setting that made the story work so well. Playing out like a daylong group therapy session, the film’s honest depiction of its five teenage characters touched a nerve in young viewers eager to see their real lives represented onscreen. Poignant and funny, “The Breakfast Club” is Hughes at his most deeply humane.

And the Worst…

5) Curly Sue (1991)

Perhaps audiences just weren’t ready for a modern-day riff on the Shirley Temple comedies of the 1930s. Or maybe the movie just wasn’t funny enough. Whatever the reason, this sappy tale of a pint-size con artist and her homeless caretaker was a rare directorial misfire for Hughes after a string of critical and commercial successes.

4) Career Opportunities (1991)

Hughes ushered out the moronic teen sex comedies of the early ’80s with his nuanced approach to character and dialogue, but this sloppy wish-fulfillment fantasy about a young janitor who discovers a beautiful girl hiding in a department store was a step in the wrong direction. Clad in a skin-tight white tanktop while suggestively riding a motorized hobby horse, co-star Jennifer Connelly is presented less like a real person and more like a joke in a “Porky’s” sequel.

3) Dennis the Menace (1993)

This live-action adaptation of the long-running comic strip is the kind of movie that parents dread taking their children to see. Shrill to the point of deafening, Hughes’ frantic script seems cobbled together from unused drafts of the far-superior “Home Alone.” As if the obnoxious tempo wasn’t bad enough, an unwelcome subplot about a burglar named Switchblade Sam made things worse.

2) Baby’s Day Out (1994)

If the sight of a lost baby crawling into traffic is your idea of a good time, then at least you’ll find one thing to enjoy in this misbegotten homage to Tex Avery cartoons. Trotting out the cliché of criminals meeting their match against children for the umpteenth time, Hughes’ screenplay for “Baby’s Day Out” is an often wordless collection of frenzied sight gags punctuated by screeching tires and screaming kidnappers.

1) Home Alone 3 (1997)

Since the idea of a 17-year old Macaulay Culkin smashing burglars on the head with bowling balls might not fly as family entertainment, writer-producer Hughes cast 8-year old Alex D. Linz as a different kid who violently confronts a group of high-tech thieves foolish enough to enter his lair. Structured like a prepubescent “Straw Dogs,” “Home Alone 3” is a 102-minute endurance test.

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