John Hughes’ body of work is diverse, multifaceted, and remarkably forthright in its consistency in terms of character. Films like Mr. Mom and Uncle Buck function like standard studio comedies, and the celebrated filmmaker only became more of a seemingly appointed studio scribe in later years on projects such as the Home Alone movies and the family-friendly Beethoven franchise, among other similarly minded projects that were given birth over the course of the 1990s. And yet it is in his directorial outpouring where many cinephiles have found emotional and spiritual succor over the years. Hughes has made certain motion pictures out of some particularly mature and nuanced comic material, such as in his classic road film from 1987, Planes, Trains and Automobiles, in addition to his work on the adult-oriented and broadly sophomoric National Lampoon’s Vacation in 1983, in addition to its immediate sequels from 1985 and 1989.

Pretty in Pink

Paramount Pictures

But more than any of the formerly mentioned works of contemporary American comedy, Hughes is perhaps most well known for his seminal series of teen comedies that he wrote and directed throughout the 1980s. Starting with Sixteen Candles in 1984, Hughes quickly established a rotating cast of young actors, pulled from an impromptu theater company that became popularly known as the Hollywood Brat Pack, and produced some of the very best coming-of-age films of all time. After establishing himself with the aforementioned sex-romp, Hughes quickly built upon his previous sophomoric excesses with the hard-hitting, emotional wallop that was and is The Breakfast Club a year later, before moving onto the equally broad (albeit intellectually shallow) Weird Science in 1985. Hughes then culminated his tenure as a director of juvenile fare in 1986 with Ferris Bueller’s Day Off, serving as a culmination of everything that he had done within the sub-genre previously with all of the flare and comic catharsis that his films have since become synonymous with.

But during the same time that Hughes was directing his swan song to the coming-of-age cinematic milieu with one of his greatest male characters as he was so timelessly portrayed by Matthew Broderick, his former female muse Molly Ringwald, who is perhaps the greater focal point of an entirely cinematic iconography, was starring in Howard Deutch’s directorial debut Pretty in Pink based on a screenplay written by Hughes. The film tells a fairly conventional Bildungsroman of a sort, wherein a poor girl from the wrong side of the tracks, literally and figuratively, falls in love with a boy from another walk of life, socially and economically, and the great rift that opens up when the two of them begin to engage in a romantic affair with one another despite the great cultural difference between their two mutually-exclusive social circles.

Ringwald, who previously starred in Sixteen Candles and The Breakfast Club under Hughes’ direction, truly comes into her own in Deutch’s film as central protagonist Andie Walsh, who is supported by the stirring, sexually ambiguous side-kick-cum-paramour Phil “Duckie” Dale (Jon Cryer) and an equally resonant and spiritually crippled father played to stunning effect by the likes of Harry Dean Stanton. Andrew McCarthy playes her presumed lover Blane McDonough with all of the stilted mannerisms inherent to the bourgeois clique, and a young James Spader plays the sneering antagonist Steff McKee with a certain malevolence specific to the 1980s era.

Hughes’ other films often get spoken of with greater reverence for their singular vision specific to the writer and the director, but it is in Pretty in Pink where a lot more of the underlying subtlety and tenuous nature of the coming-of-age narrative is truly revealed for being so painfully and inescapably transitory, despite the undeniable wounds that adolescence inevitably leaves upon us all. Whereas The Breakfast Club tells much the same tragedy to similar effect, under Deutch’s direction, and with perhaps a more dramatically nuanced honesty inherent to Hughes’ subsequent script, Pretty in Pink delivers a far more complicated version of the same thematic narrative, and the conclusion that it reaches is far more haunting and valuable in terms of realism and practicality.

Pretty in Pink

Paramount Pictures

It is often said that the one you love is never the one who loves you back, which is touched upon in the controversial ending to Deutch’s film. As the now well-known story goes, when the film was initially screened with an ending that had Andie end up romantically engaged with “Duckie,” test audiences left disappointed and a little taken aback that Ringwald didn’t choose the far more attractive, not to mention sexually straightforward and undoubtedly heterosexual, McCarthy. Ultimately the studio went with the latter ending, much to viewer approval and retrospective coherency, though Deutch did later release the opposite ending in his Some Kind of Wonderful in 1987, also featuring a script by Hughes, which told the same basic story with the gender assigned to each respective character reversed, and to equally satisfying results. And it is in this very difficult schism between the two romantic options wherein the duplicitous nature of love and affection is so accurately represented in Pretty in Pink in a way that no other Hughes film has achieved with quiet as much attention paid to the pangs of unrequited and requited love in kind.

It’s hard to pick a favorite John Hughes film. The Breakfast Club, Ferris Bueller’s Day Off, and Planes, Trains and Automobiles immediatey come to mind, though on the thirtieth anniversary of Pretty in Pink’s theatrical release the latter film holds a special resonance. Ringwald was perhaps the most enigmatic performer of the 1980s Brat Pack, and as such might be best remembered as among the very best players in Hughes’ rotating troupe of film actors. Broderick is easily remembered as the most broadly applied and grinningly post-modern performer from the writer-director’s seminal coming-of-age dramas, though Ringwald might be the most emotionally honest. Her turn in Hughes’ Sixteen Candles served to establish her name as an A-list performer in the 1980s, but it wasn’t until her role in Pretty in Pink, which is perhaps her greatest film role to date, that Ringwald truly lost and found herself within one of Hughes’ greatest cinematic works of his entire career.

Featured Image: Paramount Pictures