It was 33 years ago when the iconic film Pretty in Pink hit theaters, and it quickly became a timeless classic. In this unforgettable movie, Jon Cryer gave us the lovable and quirky Duckie Dale, stealing America’s heart alongside Molly Ringwald, the beloved star of The Breakfast Club. Together, they created a magical chemistry that turned the 1986 film into a box-office smash and a nostalgic favorite for high school teens who just can’t get enough of those unforgettable '80s movies.

A Look Back at Jon Cryer's Career on His Birthday

On Tuesday, April 16, fans around the world celebrated Jon Cryer's 54th birthday by revisiting the legacy of Pretty in Pink and how this film became a pivotal moment in his Hollywood career. Reflecting on the movie years later, Jon shared his thoughts with Entertainment Weekly. “The movie holds up great,” he said with pride. However, he couldn’t help but express his initial disappointment that his character, Duckie, didn’t end up with Andie Walsh, played by Molly Ringwald. It’s a detail that resonates deeply with fans who rooted for Duckie throughout the film.

The Evolution of Duckie Dale's Story

Back when the movie first premiered, Jon admitted he was a bit annoyed by the decision to have Andie choose Blane McDonough (Andrew McCarthy) over Duckie. “At the time, I was annoyed, because I wanted to be the guy who got the girl,” he confessed. As time went on, Jon matured and gained a new perspective on the film’s ending. Now, he believes the writers made the right call. “I do think the movie is best as it is, ‘cause I think you really do invest in that relationship,” he admitted. This evolution in his thinking highlights how much Jon has grown as both an actor and a person.

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Then and Now: The Cast of Pretty in Pink

As we celebrate Jon Cryer’s journey, it’s also a perfect opportunity to take a look at how the entire cast of Pretty in Pink has changed over the years. From Molly Ringwald’s iconic performances to Andrew McCarthy’s enduring charm, the film remains a beloved piece of cinematic history. Scroll below to see where life has taken Jon, Molly, and the rest of the cast since their unforgettable days on set. It’s a trip down memory lane that will remind you why this movie still holds a special place in our hearts all these years later.