- Ability over Appearance: Blane was written to be a Hunk with a Heroic Build. Molly Ringwald however had a say in the casting and picked Andrew McCarthy due to his attitude - claiming he's the type of guy she would fall in love with.
- Actor-Inspired Element: Jon Cryer suggested "Try a Little Tenderness" by Otis Redding for his dance. His original suggestion was "State of Shock" by Mick Jagger and Michael Jackson, but the filmmakers couldn't get the rights.
- Breakaway Pop Hit: While the movie isn't exactly obscure, it has been eclipsed somewhat by its soundtrack.
- "Left of Center" by Suzanne Vega. She launched her songwriter career at the same time (and the video shows some traces of Ringwald's clothing and hairstyle).
- "Shellshock" by New Order was a considerable success even without the connection to Pretty in Pink, in part because it was treated as a standard non-album single by the band rather than tying it specifically to the film (though the fact that it appears on the film's soundtrack album means that it isn't regarded as a true non-album release). Hell, the single's UK packaging provides zero indication that it was written for the Pretty In Pink soundtrack, likewise with Substance and other compilations that include the song.
- Cast the Runner-Up: James Spader was offered the role of Blane, but he chose to take the role of Steff instead. He finds it more fun to play the villain.
- Creator's Favorite Episode: Molly Ringwald named this as her favourite film of her own.
- Dawson Casting: Averted. Molly Ringwald was seventeen, and turned eighteen when the film was released. Jon Cryer however was twenty, James Spader twenty-five, Kate Vernon twenty-four, Andrew McCarthy and Alexa Kenin twenty-three. Kristy Swanson however was a teenager.
- Focus Group Ending: Andie originally ended up with Blaine because test audiences favored the bad boy over the childhood friendalthough cast members assert this happened because they complained that Duckie came off as too Ambiguously Gay. Some Kind of Wonderful came out the next year and essentially followed the original plot and ending with the genders reversed.
- Hostility on the Set: In spite of their chemistry on-screen, Jon Cryer has stated that both Molly Ringwald and Andrew McCarthy found him "irritating" from day one. Cryer, who describes himself as a "very outgoing person" believes his attitude was the reason he never got along with the very reserved Ringwald and McCarthy.
- Hey, It's That Place!: The movie was filmed at the same Los Angeles high school, where Grease was shot.
- In Memoriam: The movie is dedicated to Alexa Kenin and Bruce Weintraub. Kenin, who played Jena, died in New York just before the movie was released. Set decorator/production designer Weintraub died of AIDS at age 33.
- Inspiration for the Work: The genesis of this project emerged when Molly Ringwald asked John Hughes to write a movie based on The Psychedelic Furs song "Pretty in Pink", which was her favorite song at the time.
- Method Acting: James Spader shocked everyone with just how heavily he got into the character of Steff.
- Reality Subtext: Jon Cryer claims that he didn't get along with Andrew McCarthy or Molly Ringwald, lending subtext to his conflict over their relationship.
- Real Life Writes the Hairstyle: When the ending was re-shot, all of the principal cast members had to be called back. Andrew McCarthy had already lost a substantial amount of weight and shaved his head for a new role in a New York City play called The Boys of Winter. Although he wore an auburn wig, he's noticeably more gaunt in the re-shot scenes.
- Romance on the Set: Molly Ringwald was dating Dweezil Zappa (son of Frank), who plays Simon.
- Star-Making Role: For James Spader, and Jon Cryer.
- Those Two Actors: James Spader and Andrew McCarthy would work together the following year in Less Than Zero and Mannequin. McCarthy also directed several episodes of Spader's show The Blacklist.
- Throw It In!: When Duckie gets thrown into the girl's bathroom, he says regarding the tampon machine, "We don't have a candy machine in the boys' room". This was ad-libbed by Jon Cryer. He also ad-libbed the line, "His name is Blane? That's a major appliance, that's not a name".
- Unintentional Period Piece: Even by 1980s teen dramedy standards, this is pretty damn 80s. So much that if people showed up dressed like these people in a movie today, the audience would assume the characters were satirizing the 80s. There's also a lot of Duckie's dialogue (such as him saying "bogus" unironically).
- What Could Have Been:
- Jodie Foster was the first choice for the part of Andie before Molly Ringwald was cast, but turned it down due to scheduling conflicts.
- Charlie Sheen auditioned for the part of Blaine before the casting of Andrew McCarthy.
- Anthony Michael Hall and Robert Downey Jr. were considered for Duckie before Jon Cryer was cast. Hall turned down the offer due to his fears of being typecast as the geeky best friend.
- Word of Gay: Molly Ringwald told Time Out in 2009 that Duckie was gay:Duckie doesn't know he's gay. I think he loves Andie in the way that [my gay best friend] always loved me. That ending fell so flat - it bombed at all the screenings. I didn't realize it then - I just knew that my character shouldn't end up with him, because we didn't have that sort of chemistry. If John was here now, and I could talk to him, I think that he would completely acknowledge that.
Trivia / Pretty in Pink