The other Andie.
John Hughes wrote Pretty in Pink specifically for Molly Ringwald after the pair made Sixteen Candles together. But the studio, Paramount, wanted the producers to look for a bigger name. Executive producer and screenwriter Hughes and director Howard Deutch offered the part to Flashdance star Jennier Beals, who turned it down. Thankfully, the pair went back to their original choice. Incidentally, Andie awesome thrift store aesthetic was based on Ringwald's real life personal style.
The other Blane.
Charlie Sheen was in the running to play Blane, who John Hughes and the film's director saw as more of a traditional jock. But according to Andrew McCarthy in an interview for the DVD, Molly had seen him in St. Elmo's Fire. As he remembers it, she told producers something like, "That's the kind of guy I would fall in love with, not some square-jawed, hunky guy." He sent her a 4-foot tall Gumby doll as a thank you gift.
The other Duckie.
Pretty in Pink could have reunited Ringwald with her Sixteen Candles costar Anthony Michael Hall, who had already played multiple Hughes-written characters. As since reported by author Susannah Gora, after Hall passed on the part, Ringwald hoped to see it go to "somebody like Robert Downey, Jr." because "he was different and he was quirky, but it was completely imaginable that we would end up together."
The other man.
The chemistry may have been fantastic with her onscreen suitors, but Molly already had a guy at the time. Ringwald was dating guitarist Dweezil Zappa, one of the children of late iconoclastic musical legend Frank Zappa. A onetime MTV VJ, Dweezil had a small role in Arnold Schwarzenegger's The Running Man and shows up in Pretty in Pink as Andie's rocker friend, Simon. Dweezil later dated fellow musician Lisa Loeb. Molly married her second husband in 2007. They have three children.
The other Duckie song.
One of the most memorable scenes in Pretty in Pink is when the heartsick Duckman throws his very essence into "Try a Little Tenderness" by Otis Redding. All it said in the script was, "Duckie comes in lip-synching a song with great energy." Cryer's original pick was "State of Shock" by Mick Jagger and Michael Jackson. The director preferred The Rolling Stones' "Start Me Up" but they couldn't obtain the rights. For those moves, which the actor said in a 2006 interview were definitely meant to be comedic, Cryer worked closely with Kenny Ortega, choreographer on Xanadu, St. Elmo's Fire, Ferris Bueller's Day Off, and Dirty Dancing. Ortega went on to direct as well, taking on several episodes of Ally McBeal and Gilmore Girls, and directing a bunch a movies including Newsies, Hocus Pocus, and the High School Musical movies.