‘He Was The Guy I Wish I Was’: Pretty In Pink’s Jon Cryer Gets Candid About His Connection To Duckie And Why Fans Connect With The Character

Duckie Dale may not have gotten the girl in the end of Pretty in Pink —despite that controversial original ending—but actor Jon Cryer still looks up to his famous character. One of the best ’80s movies, the cult-classic teen drama from the late, great John Hughes stars Cryer as the besotted best friend of Molly Ringwald’s Andie Walsh, who is a bit too taken by preppy popular boy Blane McDonnagh (Andrew McCarthy) to reciprocate her pal Duckie’s feelings (even after that epic Otis Redding lip sync). 

We already knew how much Cryer appreciated his breakout Brat Pack role—he once dressed like Duckie in a Halloween episode of Two and a Half Men—but in a recent interview with People, the actor revealed that Duckie Dale was a “very aspirational” character for him. According to Cryer, he wished he had the confidence to live “life out loud” the way Duckie did, and that’s not all. He said:

Duckie was very aspirational for me, because he was the guy I wish I was. … I was actually decently good at this being on stage thing.’ But I never had the confidence I think that Duckie had, and I wish I did, because he really lived his life out loud in a way I could only aspire to.

 

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