A reshot ending to the film Pretty In Pink left the late, great John Hughes unhappy – and he vowed to do something about it with his next feature.

Spoilers for Pretty In Pink and Some Kind Of Wonderful lie ahead.

Few filmmakers before or since have been able to match the string of successes that John Hughes was behind in the 1980s. From 1984 to 1992, so much of what he touched turned to gold, and more than 30 years later his films have come to define an entire era.

But in amongst the bona fide classics Sixteen Candles, The Breakfast Club and Ferris Bueller’s Day Off sit a pair of films that never got quite the same level of acclaim and reverence. Both scripted by Hughes, and both directed by Howard Deutch.

The collaboration between the pair started with 1986’s Pretty In Pink. The film starred Hughes muse Molly Ringwald, and it touched upon several themes familiar to him: teen love, friendship, heartache, and a scene in which a teenage boy lip syncs to a pop song from the 1960s.

Following the story of Ringwald’s Andie as she negotiates the social strata at her high school, it’s become a cult classic in more recent times. But the production of the film was notably troubled. Ringwald and Andrew McCarthy clashed with co-star Jon Cryer, who described during an interview how they were “irritated with me from the start”. Of all the elements of the film that have aged, the character of Duckie has arguably fared the worst. Far from being the lovable goofball, viewed through modern eyes he is not only intensely irritating but also an awful friend to Andie for much of the film.

The original finale of Pretty In Pink had Andie ending up with Duckie at the prom. Test audiences reacted very badly to this though, reportedly booing their way through the scene. Hasty rewrites were ordered. McCarthy – who by then had shaved his head for a play – was given a wig to wear for the eventual reshoots. And Hughes was not a happy man with the eventual ending of the film, falling out with Deutch over it. The two would part ways on their planned next venture. As for Hughes, for his next film he wanted to in part right what he saw as the wrong of this one.

In short, he basically wanted a second crack at the same story. By this stage, he’d already hired Martha Coolidge to direct his next venture. She’d just had a sizeable hit with Valley Girl, had originally been hired to direct Hughes’ next project, Some Kind Of Wonderful, and had she stayed, the film would likely have been notably different from the one we got. But she would never get the chance to direct the movie, dropped from the project before it really got going. As it turned out, Pretty In Pink was a bigger hit than expected. Hughes hired Deutch to direct after all.

Some Kind Of Wonderful, then, was essentially Hughes and Deutch’s second crack at the same story, to the extent that Hughes originally tried to cast Ringwald and McCarthy as Amanda and Keith respectively. But they both refused the roles, with Ringwald telling The Atlantic “I declined because I felt like the script wasn’t strong enough and was too derivative of the other films I’d already made with John”.

This reportedly soured Ringwald and Hughes’ working relationship and sadly they never made another film together. McCarthy was similarly critical, saying “it seemed like we just kept making the same movie again” And while to an extent that is true, and although not as well remembered as Pretty In Pink, for this writer it’s the better film.

In it, Eric Stoltz, Mary Stuart Masterson and Lea Thompson play the central threesome, all of whom play characters named in part by way of tribute to The Rolling Stones: Keith Richards, Charlie Watts and the song Miss Amanda Jones. In many ways the film adheres to similar clichés often seen in teen films of the 80s: the boy who is in love with a rich girl and his ostracised best friend. But the subtleties Hughes gave his characters ensured that they always rose above the stereotype, with even school bully Duncan given a character arc.

Thompson’s Amanda Jones isn’t actually rich, but due to her social circle she is deemed wealthy by association, and this is perhaps where the film differs most from Pretty In Pink. Where Pink’s characters were heightened and to a certain extent not straying from the stereotypes. I don’t think that’s the case in Some Kind Of Wonderful.

Pretty much everything about the film is a mirror image of Pretty In Pink. The genders are reversed and the basic plot structure remains the same, but I think the main difference between the two films is that in Wonderful the characters feel more real. There is a genuine chemistry between Stoltz and Masterson that isn’t quite as strong between Cryer and Ringwald. The main reason for this – for me at least – is that the various relationships are afforded the space in the screenplay to evolve naturally as opposed to Pretty In Pink’s plot leading to its rather abrupt ending. It might be more melodramatic in execution, especially in some of the latter scenes where the characters bare their souls to each other, but it at least attempted to dig that little bit deeper into the conundrums and complexities of the teenage psyche.

Two sides of the same coin, Pretty In Pink and Some Kind Of Wonderful make for an intriguing double bill. While they both tell almost identical stories, it’s the different avenues Hughes takes along the way that make them distinct entities. And whether you prefer one or the other, what stands out and indeed the reason why these films have endured is Hughes’ skill at crafting fully rounded characters who linger in the memory long after the final frame.

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