Jon Cryer on Pretty in Pink, Two and a Half Men, and Lex Luthor

During a live NostalgiaCon conversation with Nerdtropolis, Jon Cryer opened up about four decades of memorable roles, career-changing decisions and the unexpected full-circle moment that turned Superman IV’s Lenny Luthor into Lex Luthor.

Jon Cryer has built a career across some of film and television’s most recognizable titles, from Pretty in Pink and Two and a Half Men to Superman IV: The Quest for Peace and Supergirl.

During a live Nerdtropolis interview at NostalgiaCon, Cryer looked back on Duckie, Alan Harper, and Lex Luthor while sharing the career decisions and unexpected connections that shaped those roles.

He also opened up about choosing Two and a Half Men over Battlestar Galactica, his early history with Charlie Sheen, the lost alternate ending of Pretty in Pink, and why accepting Lex Luthor became a deeply personal full-circle moment.

Jon Cryer on Nostalgia and Connecting With Fans

For Cryer, nostalgia is ultimately about the rare opportunity an actor gets to become part of someone else’s memories.

“You don’t have a divine right to get a job,” Cryer said. “You’re lucky to get a job and then to have something that actually resonates with people, and that they become fans of; again, you’re incredibly lucky for that as an actor.”

Why Pretty in Pink Still Connects

Pretty in Pink became one of the defining movies of Cryer’s early career, but its continued popularity has surprised him.

Cryer recently attended a screening in New York where a large group organized by NYU came to see the movie. Watching a younger generation respond to the film reinforced how unusual that kind of longevity can be.

“Teenagers now see it, and it connects with them now,” Cryer said. “Actors need to feel grateful for the times when they connect with their audience because it’s so rare, and we don’t get to choose when that happens.”

What Extended Family Still Means to Cryer

Cryer carries the same appreciation for projects that do not last nearly as long.

Cryer starred opposite Donald Faison and Abigail Spencer in Extended Family, which ended after one season. Looking back, Cryer said the opportunity to perform a sitcom in front of a live audience remains special.

“Doing a live show in front of an audience is an incredible gift, and there’s not a lot of them on now,” Cryer said. “Anytime that you get a chance to do that, to do a live audience show, it’s just incredibly precious. So I’m just grateful.”

Cryer also made it clear he would be open to reuniting with Faison on Scrubs.

“Dude, I’m right here,” Cryer joked when the possibility of a cameo came up.

Jon Cryer on Playing Duckie in Pretty in Pink

Duckie Dale became one of Cryer’s signature characters, but the confidence audiences saw on screen was not necessarily something Cryer recognized in himself at the time.

“Duckie was the guy I wanted to be in high school,” Cryer said. “The guy who was kind of big and broad and didn’t care what anybody thought about him. I wished I was that guy. I was not that guy.”

Cryer described himself as shy and already immersed in theater as a teenager.

How Cryer Related to Duckie

One part of Duckie’s personality came from familiar emotional territory.

Cryer said he had experienced plenty of unreturned crushes and understood the feeling of being close friends with someone while hoping the relationship could become something more.

“I had a lot of crushes on girls that were not reciprocated,” Cryer said. “I had wonderful female friends who I had crushes on.”

He jokingly summed up that chapter of his life another way.

“I lived in the friend zone,” Cryer said. “I had a rental unit in the friend zone. That was my life.”

Why He Sees Duckie Differently Today

Rewatching Pretty in Pink has given Cryer a slightly different perspective on the character.

Rather than focusing entirely on Duckie’s disappointment, Cryer now appreciates how completely the character embraces who he is.

“He was trying so hard,” Cryer said. “He wasn’t ashamed of being earnest. He didn’t worry about being cringe. He was Duckie. He was a ridiculous person, and I love that about him.”

Jon Cryer on the Pretty in Pink Alternate Ending

Few subjects surrounding Pretty in Pink have generated more discussion than its original ending.

Cryer explained that the first version did not end with Andie and Blane together.

Instead, Andie attended the prom, heard Blane’s apology, and ultimately danced with Duckie to David Bowie’s “Heroes.”

Why Test Audiences Changed the Ending

The original ending didn’t work for the audiences who saw it.

According to Cryer, viewers had become invested in the romantic relationship between Molly Ringwald’s Andie and Andrew McCarthy’s Blane.

“Audiences really bought into the love relationship between Molly Ringwald’s character and Andrew McCarthy’s character,” Cryer said.

The ending was eventually reshot with Andie and Blane together.

The debate continued partly because the movie’s novelization had been written using the earlier script and preserved the original conclusion.

Why Cryer Is Fine With Andie Choosing Blane

Despite years of debate over whether Andie should have chosen Duckie, Cryer said the original ending was not necessarily supposed to establish them as a romantic couple.

“It was always about their friendship,” Cryer said. “So I’m okay with it. I’m okay with it as it is.”

His bigger issue with the final version comes from Duckie suddenly noticing another girl at the prom.

Cryer said he wishes the movie had established some previous interaction between the two characters so the moment did not appear completely out of nowhere.

Why the Lost Ending May Never Be Seen

Fans hoping to eventually see the original footage could be out of luck.

“I’d love to see it,” Cryer said. “As far as I know, the alternate ending does not exist anymore.”

Cryer said the director had looked for the footage but couldn’t locate it.

Jon Cryer on Friends and Battlestar Galactica

Several major projects could have sent Cryer’s career in completely different directions.

Two of the biggest were Friends and Battlestar Galactica.

Why He Says Friends Was Never Really His

Cryer was performing in London when he received a late-night call from Friends executive producer Marta Kauffman about auditioning for the series, then known as Six of One.

He recorded an audition the following morning with a British casting director and sent the tape to the United States.

It never arrived in time. “It got stuck in customs and did not arrive until after they had already cast Matthew Perry,” Cryer said.

Despite how close the story can sound, Cryer does not believe he narrowly missed becoming Chandler Bing.

“They had been trying to cast Matthew Perry for months,” Cryer said.

Perry had been attached to another pilot, and once the situation cleared, Cryer said the producers could bring in the actor they already wanted.

“So I never would have gotten Friends,” Cryer said.

How Close He Came to Battlestar Galactica

His experience with Battlestar Galactica was much different.

Cryer loved the script for the reimagined series and auditioned for Gaius Baltar.

He had a strong meeting with Ronald D. Moore, and the network wanted him to test for the role.

The problem was timing. Cryer was also testing for Two and a Half Men on the same day.

“I had to pick whether to go in on Two and a Half Men or Battlestar Galactica,” Cryer said.

Why He Chose Two and a Half Men

Cryer ultimately chose Two and a Half Men.

“It was a flip of the coin,” he said. James Callis went on to play Gaius Baltar, while Cryer’s decision eventually resulted in a 12-season run as Alan Harper.

“I have no regrets, obviously,” Cryer said. “Two and a Half Men was great fun for me.”

Jon Cryer on Charlie Sheen and Two and a Half Men

Cryer already had a history with Charlie Sheen before Two and a Half Men.

The pair previously appeared together in Hot Shots!, and the familiarity became important when they reunited for the CBS sitcom.

How Hot Shots Helped Their Chemistry

Cryer remembered immediately feeling comfortable reading with Sheen.

“The first time we read it, it was 100% clear that we were the guys to do this,” Cryer said.

Immediate chemistry like theirs does not happen on every project.

“Sometimes you know, and sometimes you got to search around for it,” Cryer said. “There was none of that with this. It worked immediately.”

Having Sheen attached to the project became one of the reasons Cryer felt confident choosing the sitcom over Battlestar Galactica.

When Cryer Knew the Sitcom Was a Hit

A successful pilot did not automatically convince Cryer the series would last.

He had been through enough television productions to know even pilots that feel great can disappear quickly.

The real realization came after Two and a Half Men began airing on Monday nights following Everybody Loves Raymond.

By the third episode, Cryer said their ratings were already approaching those of the established hit airing before them.

“We thought, okay, we’re gonna be fine here,” Cryer said.

They were.

Cryer ultimately played Alan Harper for 12 seasons.

Jon Cryer on Alan Harper After 12 Seasons

Playing one character for more than a decade inevitably leaves an impression.

For Cryer, one quality in Alan Harper remains especially familiar.

Why Alan Harper Still Feels Familiar

Cryer identified with Alan’s determination to maintain a little dignity regardless of how badly everything around him was falling apart.

“He was always sort of trying,” Cryer said. “He was always thwarted.”

Everything could go wrong for Alan, but he would keep moving forward.

“He always tried to have some dignity through it,” Cryer said. “And that’s me. I try to have some dignity no matter how goofy things get.”

Jon Cryer on What Made Charlie Sheen So Funny

The history surrounding Two and a Half Men can sometimes overshadow how effectively Cryer and Sheen worked together as comedy partners.

Asked what made Sheen such a strong performer, Cryer immediately pointed toward his timing.

“Charlie’s amazing in that he has amazing timing,” Cryer said.

Sheen Had Sitcom Timing Built Into Him

Cryer said he once asked Sheen whether he had developed his timing through theater or stage work.

He had not. Instead, Cryer believes Sheen absorbed the rhythm through years of watching sitcoms.

“He just grew up on sitcoms, loved them the same way that we all loved those sitcoms and just had that sort of built into his brain,” Cryer said.

Sheen also had an impressive ability to remember dialogue.

The series frequently rewrote material throughout rehearsals, meaning the cast regularly had new lines to learn.

Cryer remembered Sheen spending nights watching sports and still arriving prepared the following day.

“He just had this incredible facility for memorizing lines,” Cryer said.

Jon Cryer on Superman IV and Lex Luthor

Cryer’s path through the Superman universe might be the most unusual full-circle story of his career.

He first joined the franchise as Lenny Luthor in Superman IV: The Quest for Peace, appearing alongside Gene Hackman’s Lex Luthor.

More than three decades later, Cryer was asked to become Lex himself.

Why Christopher Reeve’s Superman Inspired Him

Cryer was already deeply invested in Superman before joining the fourth film.

He remembered seeing Christopher Reeve’s original movie as a teenager and becoming captivated by it.

“The original Superman came out when I was 14,” Cryer said.

The movie famously promised audiences they would believe a man could fly.

“And they did,” Cryer said. “They absolutely did it.”

His love for the original film made joining Superman IV especially exciting.

“They got Gene Hackman back, and they got Margot Kidder back,” Cryer said. “They did this amazing job reassembling the cast from the original.”

What Went Wrong With Superman IV

The excitement did not last. According to Cryer, production problems started becoming obvious within weeks.

Money became an issue, and significant portions of shooting began disappearing from the schedule.

Cryer said money intended for Superman IV was being moved toward Masters of the Universe, which was being produced at the same time.

“They started cutting out whole weeks of shooting,” Cryer said. The final movie left him disappointed.

“I always felt like I kind of let down the Luthor family,” Cryer said.

His disappointment with the film became important decades later when another opportunity unexpectedly arrived.

How Supergirl Brought Him Back to the Luthor Family

The road back involved another recurring piece of Cryer’s life: theater camp.

A friend from the same summer camp Cryer had attended told him he was about to receive an offer for something he would probably want to accept.

Another former camper had eventually become a producer on Supergirl.

The offer was Lex Luthor. “She called me, and I was stunned,” Cryer said. “I was absolutely stunned.”

Jon Cryer on Accepting the Lex Luthor Role

For Cryer, returning to the Luthor family offered a chance to revisit something that had never felt completely finished.

Why He Worried About Playing Lex

Cryer immediately connected the opportunity to his disappointment surrounding Superman IV.

“Now is my chance to fix it,” Cryer said, “and to really do Lex in a way that I thought he deserved to be done.”

There was still one major concern. Cryer had spent more than a decade playing Alan Harper.

He knew exactly how some fans might react to seeing the actor behind Alan suddenly transformed into one of Superman’s greatest enemies.

“I knew that people were not gonna be happy with Alan getting cast as Lex Luthor,” Cryer said. “The internet is not gonna be happy about that at all.”

The potential fan reaction initially left Cryer on the fence.

How a Memorial Service Led to His Decision

The final decision came in an unlikely setting. Cryer was attending a memorial service for a friend who had been a theater teacher and was connected to the same summer camp that had already played such an unusual role in his life.

During the service, messages about Lex Luthor kept arriving on his phone.

Cryer initially refused to respond. “I’m not gonna answer the texts during a memorial service,” he said.

The memorial kept going. Because so many of the speakers were actors, Cryer joked that everyone was particularly long-winded. There were speeches, songs and performances as the service stretched toward three hours.

Eventually, the Lex Luthor situation could not wait.

“Finally, I had to take the call,” Cryer said. “I was like, that’s it, I gotta take this part.” He accepted Lex Luthor during the memorial service.

Why Lex Luthor Became a Full-Circle Role

Some connections across an actor’s career only become obvious years later.

This was not one of them. “The Lex Luthor thing, I absolutely appreciated the full circle,” Cryer said.

The actor who once stood beside Gene Hackman as Lenny Luthor had eventually inherited the Lex Luthor name himself.

Jon Cryer on Gene Hackman and Christopher Reeve

Asked where he would go if he could use a DeLorean to spend five minutes with himself on any project from his career, Cryer initially gave the most practical answer possible.

“Buy Apple stock.” His real choice was Superman IV.

Why He Would Return to Superman IV

“I would say, ‘Hey man, don’t worry about this. You got this,’” Cryer said.

There was another reason he would return to the set. Gene Hackman.

What He Remembers About Gene Hackman

Cryer described Hackman as surprisingly kind to him during production and remembered using the opportunity to ask the acclaimed actor plenty of fan questions.

One was about Hackman’s favorite role. According to Cryer, the answer was his appearance in Young Frankenstein.

Cryer also asked which complete movie from his career was his favorite. Hackman chose The Conversation.

“I would love to have spent a little more time with him,” Cryer said.

How He Remembers Christopher Reeve

Cryer also remembered Christopher Reeve fondly. Reeve had already become Superman in Cryer’s eyes long before the two worked together.

When their paths finally crossed, Cryer found someone who lived up to that admiration.

“He was lovely to everybody,” Cryer said.

Jon Cryer on What He Wants to Do Next

NostalgiaCon offered plenty of reasons to look backward, but Cryer is not finished searching for something new.

Asked what could still make him feel like a young actor taking on something unfamiliar, Cryer immediately turned toward theater.

Why a Broadway Musical Is Still on His List

Cryer said he was performing off-Broadway in The 25th Annual Putnam County Spelling Bee and described the experience as “so much fun.”

He has performed in Broadway plays before, but one major theatrical experience remains on his list.

“I’ve never done like a big Broadway musical,” Cryer said. “I’d probably love to do something like that. That would be a very exciting thing.”

The Broadway discussion naturally led to the suggestion of turning Superman IV into a musical.

Cryer quickly pointed out Superman already has a musical history on Broadway, proving once again how deeply his career has crossed between theater, television, film, and superheroes.

Duckie continues finding younger audiences. A near-miss with Battlestar Galactica led to 12 seasons of Two and a Half Men. Working with Charlie Sheen on Hot Shots! helped lay the groundwork for one of television’s most successful comedy partnerships. Playing Lenny Luthor in a troubled Superman sequel ultimately gave Cryer another chance with the mythology as Lex Luthor.

At NostalgiaCon, those seemingly disconnected chapters became parts of the same story.

After decades of memorable roles, Cryer is still looking toward whatever comes next.

---

Read more News and Subscribe to our YouTube.