When the anniversary of a film hits it is always nice to revisit why it remains a classic. Yet sometimes its a bit more fun to randomly happen on a film again organically. This is what happened to me with Pretty in Pink, the John Hughes penned 1986 film now turning the big 3-0. Directed by then first timer Howard Deutch who would go on to direct Some Kind of Wonderful in 1987, Pretty in Pink was Hughes’ tenth screenplay. The film is also his third and final with 1980s it girl Molly Ringwald whose pop culture status is synonymous with the high school set cinema experience. what is timeless and still refreshing about Pretty in Pink is its candor. Where The Breakfast Club gave us the social microcosms of high school and the judgement associated with labels, Pretty in Pink gives us those under the microscope of money. Where Sixteen Candles gives us the antsy terror of first love blossoming, Pretty in Pink gives us love with a side serving of social shame. Of course, I am not implying that the other films lack these themes, more that this film directly addresses economic discrepancy between potential partners still relevant today.

Firstly, Ringwald’s Andie is an intelligent, creative, and supportive character. It is rare now to see this age depicted with such kindness and gumption. Hence why recent roles like Shailene Woodley’s in The Descendants (2011) felt fresh. Youth is not synonymous with dumb or careless in Hughes’ world. Andie’s relationship with her father (Harry Dean Stanton) remains three dimensional despite time, the ‘single dad from walking out’ still an A-typical choice. Their Ringwald’s success was and is her ability to seem ordinary yet extraordinary within the minutia of high school. Like Jon Cryer’s Duckie, she does her own thing despite social repercussions. This includes her direct conversations with potential boyfriend Blane (Andrew McCarthy). The struggle to have these direct talks about how their economic situations affect their potential pairing is the root of the timelessness of the story. Like the best moments of Dawson’s Creek, when teenagers face their fear and ASK questions, Pretty in Pink reminds us that teenagers (and even adults) are still figuring things out and that is okay.

One of the main takeaways from revisiting a film can also be remembering an actor in youth. James Spader whose worked consistently, but never maintained the golden boy looks of the 1980s, is a luring presence here. His stalker-like attempts on Andie echo of a 1980s fraught with sexual harassment to women in the work place. His feathered do and linen looking suits make like he is playing dress up in his father’s closet. He’s all Miami Vice, misogyny included. Next to Cryer’s Duckie he reminds us that all sides of money can be miserable. Duckie though remains frantically earnest. His energy and look seem a clear precursor to Matthew Broderick’s Ferris Bueller.

Pretty in Pink remains a clever look at high school through a lens of understanding coming from the teens rather than the adults. There is nothing staggering about the film-making, but Deutch clearly new the power of Ringwald’s face. Her pout and open clear expression give Andie the likable force to have her moment, her way. In a generation not plagued by texts and social media, but rather sitting by the phone, Pretty in Pink is a fun reminder that ultimately: who cares what people think.

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