When Pretty in Pink premiered in theaters 33 years ago, Jon Cryer stole America’s heart as Duckie Dale alongside The Breakfast Club actress Molly Ringwald. Together, the duo made the 1986 movie a box-office success and a nostalgic film for high school teens, who can’t get enough of ’80s movies.
In honor of Jon’s 54th birthday on Tuesday, April 16, we remember Pretty in Pink and how the film helped to boost his Hollywood career. “The movie holds up great,” Jon previously told Entertainment Weekly, but said that he was very disappointed that his character didn’t get Andie Walsh (Molly) in the end.
“At the time, I was annoyed, because I wanted to be the guy who got the girl,” he said. Jon didn’t understand why the movie ended the way it did until he got older. Now he believes the writers made a good decision to have Andie pick Blane McDonough (Andrew McCarthy) instead of him. “I do think the movie is best as it is, ‘cause I think you really do invest in that relationship,” he admitted.
Scroll below to see Jon, Molly and the rest of the cast then and now!