Jon Cryer on His 'Aspirational' “Pretty in Pink ”Character: 'He's the Guy I Wish I Was' (Exclusive)

The Emmy-winning actor tells PEOPLE why he admired the character that made him famous and how he’s still approached about Duckie decades later

Almost three decades after he starred in the Pretty in Pink, Jon Cryer is still recognized for the role that catapulted him to stardom.

In the 1986 teen classic, Cryer famously played Duckie, the quirky high school classmate of Andie (Molly Ringwald), who falls for the dreamy rich guy Blane (Andrew McCarthy). While Andie and Blane ultimately end up together by the film’s end, Duckie left an indelible impression of his own as a lovable outsider who provided the film’s most memorable moment: a lip-synced dance to Otis Redding’s “Try a Little Tenderness.”

“Duckie was very aspirational for me, because he was the guy I wish I was,” says Cryer, who currently stars in the new NBC sitcom Extended Family.

Related: 30 Things You Might Not Know About 'Pretty in Pink', 30 Years Later

Being a self-proclaimed “theater dork” at the Bronx High School of Science made Cryer, 58, realize he was, what he describes as a "funny person.” “I was actually decently good at this being on stage thing,’” he explains. “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.”

Cryer admits he "felt like an outsider" himself during high school. Besides falling in love with one girl during his senior year in high school — "that didn't end up working out," he says — he didn't date much during that time.

“I think that really is a universal experience for most people,” he continues. “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."

While Cryer has since gone on to other successful projects, including the CBS sitcom Two and a Half Men, which ran from 2003 to 2015 and earned him two Emmy Awards, it’s the role of Duckie that people return to time and again.

The actor, for his part, has been more than happy to revisit the character himself, dusting off his now-famous lip-synced number and performing it on the Late Late Show with James Corden in 2015. He also reunited with Ringwald, 55, and Annie Potts, who portrayed Iona in the film, for a reunion with Entertainment Weekly in 2020.

Related: Molly Ringwald Wishes She'd Kept Her Iconic Prom Dress from 1986 Film Pretty in Pink (Exclusive)

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But perhaps it’s the feedback he hears from avid Pretty in Pink viewers that has meant the most with him. Regardless of the huge shift in societal values and pressures since the ‘80s, Duckie remains a character many still see a bit of themselves in.

“I've heard it from people [that it’s] because there's this outsider thing,” he explains. “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.”

For more on Jon Cryer, pick up the latest issue of PEOPLE, on newsstands Friday, or subscribe here. 

Extended Family returns Tuesday, Jan. 2 at 8:30 p.m. ET on NBC.

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