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John Hughes wanted Anthony Michael Hall to play Duckie

Anthony Michael appeared in John Hughes’ directorial efforts Sixteen Candles, The Breakfast Club and Weird Science. When Pretty in Pink came around, Hughes wanted Hall to play Duckie, opposite his two-time former co-star Molly Ringwald. However, Hall thought the part was too similar to his Sixteen Candles role The Geek, so he declined Hughes’ offer.

The movie took its title from the song by The Psychedelic Furs

Oftentimes theme songs with the title in them written specifically for the film, but this wasn’t the case with Pretty in Pink. English post-punk band The Psychedelic Furs first recorded the song in 1981; Molly Ringwald played the song to John Hughes, who was inspired to build the screenplay around it. The Psychedelic Furs then recorded a new take on the song for the film.

The movie made the wrong song famous

Despite the prominence of the title track, Pretty in Pink fans latched on to a different song from the soundtrack that wasn’t intended to be the standout piece: If You Leave by Orchestral Manoeuvres in the Dark, which plays at the end of the movie.OMD wrote the song in one go in just two days, and were surprised when it proved hugely popular.

Charlie Sheen was the first choice to play Blane

In Hughes’ screenplay, the character of Blane was written as a hyper-masculine jock, and with this in mind the filmmakers were originally considering more conventionally macho actors to play the part. One well-known actor who came close to being cast in the role was Charlie Sheen, who later in 1986 made a brief but memorable appearance in another John Hughes film, Ferris Bueller’s Day Off.

Ringwald forced the producers to cast the ‘twerpy’ Andrew McCarthy

Molly Ringwald was allowed to have some say in the casting of Blane, and when St Elmo’s Fire star Andrew McCarthy auditioned, Ringwald decided that he was the one. The producers and director were not at all keen, however, as they saw McCarthy as a “twerpy” guy. Still, Ringwald held her ground until they cast him.

Andie originally chose Duckie at the end

Pretty in Pink originally ended with Andie choosing Duckie over Blane. However, test audiences responded badly to this match-up. The movie was quickly changed, with a new ending added to allow Blane and Andie to get together. Producers also added a happy ending for Duckie, which basically consisted of Duckie being stared at and immediately getting over his Andie crush.

McCarthy looks gaunt, wears a wig for his re-shot scenes because he’d since entirely changed his look for a play

By the time reshoots were called, Andrew McCarthy was performing in a play which he had lost a significant amount of weight and cut his hair. Look closely and you may notice in the scenes near the end of the movie that Blane is noticeably more gaunt, as well as sporting a not entirely convincing hairpiece.

Ringwald fainted when she shot the original ending

Jon Cryer has suggested that Pretty in Pink’s original ending may not have gone down well with test audiences because Molly Ringwald was sick with stomach flu when they shot it. Cryer says she fainted on him, and the crew had to scramble to find shots they could film around her. As this footage is now believed lost, we may never know the truth.

Cryer later reprised the role of Duckie twice

Duckie remains Jon Cryer’s most fondly-remembered role, and he’s dressed up as Duckie twice on film since. First off, Cryer dressed as Duckie for Halloween in an episode of Two and a Half Men, to the delight of the audience. Later, Cryer then dressed up in the costume one more time to battle James Corden in a lip-sync duel.

Ringwald and Hughes planned a follow-up movie, but never worked together again

Credit: Kevin Winter via Getty

Molly Ringwald and John Hughes planned to work together again on an movie called Oil and Vinegar, which would also have starred Matthew Broderick. Pretty in Pink’s director Howard Deutch would have called the shots, but he decided to drop the project because he was exhausted from shooting three films for Hughes back-to-back (the other two being Some Kind of Wonderful and The Great Outdoors).

Ringwald thinks Duckie was secretly gay

Molly Ringwald has her own theory about why Duckie’s infatuation with Andie never worked out: she thinks Duckie was actually gay, but had yet to realise that about himself. Many fans have embraced this, feeling it explains Duckie’s flamboyance. However, both director Howard Deutch and actor Jon Cryer have said they “respectfully disagree” with Ringwald on this matter.

John Hughes’ next movie allowed Pretty in Pink’s original ending to play out

The year after Pretty in Pink, John Hughes and Howard Deutch made the similarly themed Some Kind of Wonderful, which centres on another love triangle: this time, male underdog Eric Stoltz is torn between his quirky BFF Mary Stuart Masterson and popular girl Lea Thompson. This time around, Pretty in Pink’s original outcome played out with the two friends becoming a couple at the end.

The film shares a high school with 1978’s Grease

If the interior of Pretty in Pink’s high school starts to look familiar to you, that’s because it also features in another classic coming of age movie. Some scenes of 1978’s beloved musical Grease was shot at the very same location, John Marshall High School in Los Angeles. Years earlier, school scenes for James Dean classic Rebel Without a Cause were also shot there.

Molly Ringwald and Andrew McCarthy didn’t get along with Jon Cryer

The chemistry between Pretty in Pink’s main characters might seem very real, but in reality Molly Ringwald and Andrew McCarthy found it hard to get along with Jon Cryer, who played Duckie. Cryer admits he was just as exuberant as Duckie off-camera, which may have put off his more reserved co-stars. Happily, all three of them seem to get along fine today.

The film features two tragic tributes at the end

Pretty in Pink’s closing credits tribute is dedicated to Alexa Kenin, who plays Jena. Kenin tragically died without ever seeing the finished film, as she was murdered in New York shortly before it was released. In another tragic twist, the movie also features a dedication to production designer Bruce Weintraub, who sadly died of AIDS shortly after production on the film finished.

James Spader turned down the chance to play Blane

James Spader was one of John Hughes’ first choices to play Blane. However, the actor requested the role of bully Steff instead. When asked why, Spader responded that it was always more fun to play a villain. He has since taken more notable villain roles in TV’s The Blacklist, and the title role in Avengers: Age of Ultron.

Duckie’s ‘candy machine’ line was ad-libbed

When Duckie is thrown into the women’s bathroom by bullies, Duckie quickly remarks to the girls in there, “We don’t have a candy machine in the bathroom,” pointing to a tampon dispenser. The line soon became one of the most memorable parts of the film, since it perfectly showcased Duckie’s charisma and wit.

There is a nod to another classic film of the era

Annie Potts appears in Pretty in Pink as Iona, manager of Trax, the record store where Andie works part-time. The previous year, Potts landed her most famous role as secretary Janine in Ghostbusters, in which she famously roars into a telephone “Ghostbusters, what do you want?!” Pretty in Pink pays homage to this, with Iona answering the phone and saying, “Trax, what do you want?!”

The film is Molly Ringwald’s favourite of her own

In more recent years, Molly Ringwald has spoken critically of some of her work with John Hughes, pointing out the problematic elements of Sixteen Candles and The Breakfast Club. However, Ringwald has called Pretty in Pink her favourite film of her own, not least as John Hughes really tailored the part to her based on many hours of conversation between the two.

Ringwald hated the pink dress

Given the title, the pink dress Andie wears at the climax should be a show-stopper. However, Ringwald hated the prom dress she had to wear, finding it frumpy and uncomfortable. Even diehard fans of the film are divided about the dress, with some agreeing that it looks like a pink potato sack.