Cryer says he ultimately developed compassion for McCarthy after learning he was “was battling his own demons” on the 1986 film shoot.

Jon Cryer says he and Andrew McCarthy had ‘all kinds of issues’ filming Pretty in Pink

Cryer says he ultimately developed compassion for McCarthy after learning he was "was battling his own demons" on the 1986 film shoot.

By Ryan Coleman

Ryan Coleman

Ryan Coleman is a news writer for with previous work in MUBI Notebook, Slant, and the LA Review of Books.

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June 7, 2026 8:27 p.m. ET

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Andrew McCarthy, Molly Ringwald, and Jon Cryer in 1986. Credit:

Paramount/Kobal/Shutterstock

- Jon Cryer is opening up about his rocky road to friendship with Andrew McCarthy in a new interview.

- Cryer initially thought his *Pretty in Pink *costar was a "dick," citing "all kinds of issues" on the 1986 film set.

- More recently, Cryer told *Page Six *he was able to develop compassion for McCarthy after learning he was "battling his own demons."

It turns out there was a bit of truth to the romantic rivalry at the heart of *Pretty in Pink*.

Jon Cryer, who starred as the insecure geek Philip "Duckie" Dale in John Hughes' classic teen drama, is opening up about his rocky relationship with Andrew McCarthy, who played the impossibly cool Blane McDonnagh.

In the 1986 film, Duckie and Blane compete for the affections of star Molly Ringwald's Annie Walsh, leading them to several tiffs and spats. But off screen, it was McCarthy himself who rubbed Cryer the wrong way.

"I thought he was aloof and just a dick," Cryer told *Page Six* on Saturday. "We had all kinds of issues."

Andrew McCarthy in 2024; Jon Cryer in 2024.

Cryer remembered once getting "really mad" at Ringwald and McCarthy for giggling off screen while he was trying to film a serious close-up. "I found out that the director asked them to do that because he wanted me really mad for the scene. But at the time, I didn't know."

This would prove to be only the tip of the iceberg when it came to the unseen forces that really drove a wedge between Cryer and McCarthy. "I didn't know that he was going through; he was battling his own demons and had a fractured family relationship with his dad. And he was already starting to have issues with alcohol... None of this I knew about at the time, so of course he was aloof. He was just trying to keep it together on a really big job," Cryer explained.

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McCarthy was battling a serious problem with alcohol at the time. The actor told ABC News in 2004 that he had his first drink at 12 or 13 years old. What followed was a dangerous dependency that landed him in rehab not long after *Pretty in Pink *wrapped.

"In 1992, I was in an alcohol rehab in Minnesota, and I was all played out. I was 29 years old and I was just done. I had made a mess of everything," he reflected in May.

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Reminiscing on the 40th anniversary of *Pretty in Pink *with* **The Hollywood Reporter** *in March, McCarthy said that he initially found his character to be "a jerk," and spoke at length about his on-set insecurity.

"Molly has said this publicly so I'm not talking out of school, but she had a bit of a crush on me at the time, which I didn't reciprocate." It wasn't a lack of mutual attraction, but because McCarthy was "so scared and insecure that I kept pulling back. My fear manifested as aloofness. She thought I was dismissing her when really I was just trying to get through my days because I was the new kid here and I didn’t want anyone to see I was insecure."

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