‘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

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Written By Maya Cantina

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.

He also revealed that he based the beloved character off “several of [his] friends growing up,” including a friend named Artie who had a “ridiculous pompadour,” a similar hairstyle to what Cryer sports in the Hughes flick. He shared:

I think that really is a universal experience for most people. I don’t think most people go through high school thinking, ‘I was the sh–. Everybody really dug me in high school.’ But Duckie was … a bit of a conglomeration of several of my friends growing up. I had a friend named Artie who had this ridiculous pompadour. I stole some of the sayings of my friend David, who would go, ‘Do I offend?’ And so he was a great way to represent for my peer group.

The Lex Luther actor went on to say he felt like “an outsider” during his own high school years, but that very otherness is why he thinks Pretty in Pink and Duckie’s relatability have endured in the nearly four decades since the film’s release:

I’ve heard it from people [that it’s] because there’s this outsider thing. I’ve found a lot of the gay community approached me saying, ‘That character meant a lot to me. I really felt like that was a relationship that was very similar to what I went through.’ And that’s amazing to feel like it resonated in that way for people, because you try to make a story that is just honest, and when that honesty really touches people, you feel like you did your job.

Joining Cryer’s long list of characters is Jim Kearney, the lead of the new NBC sitcom Extended Family, which follows a couple trying to navigate an amicable divorce and continuing to raise their kids at the family home. You can watch him in his newest role with episodes of Extended Family on Tuesdays at 8:30 p.m. ET on NBC, following Night Court

Still, even though Jon Cryer has had and continues to have plenty of work in the decades since Pretty in Pink, it’s clear that Duckie Dale remains a favorite both to audiences and the actor himself. 

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