A glance at Jon Cryer’s childhood shows he was long destined for the limelight. He comes from a family of actors, and even starred alongside his mother in 1987’s Hiding Out, where the pair played an aunt and nephew. But Cryer’s best-known early work was Pretty in Pink, where he stars as the lovelorn Duckie, always dressed to kill. He then went on to try out a wide range of TV roles, all unsuccessful, before he landed the part of Alan Harper in Two and a Half Men.

Running from 2003 to 2015, this show transformed the careers of Cryer and his close friend and co-star Charlie Sheen. But while Sheen was written out of the show and entered drug rehabilitation after arguments with producers, Cryer saw the series through to the end and has maintained his status as a small-screen star with the role of Lex Luthor in Supergirl.

Here are 20 things you may not have known about this star.

20. His audition tape for Chandler Bing got stuck in the mail

It may surprise you to learn that early in his career, Jon Cryer was invited to audition for Friends.


He was performing in a London play at the time, when he received a call from the producer Marta Kauffman.

She asked him if he would be interested in a show called Six of One – which would eventually become Friends.


Eagerly, Cryer teamed up with the British casting director and recorded an audition tape for Chandler Bing.

However, when it was posted to the USA, Cryer’s tape was held up at Customs and failed to reach the creators in time.


Amid this mishap, Cryer lost the famous role to Matthew Perry. He would have to wait another decade before making his name in TV with Two and a Half Men.

19. His front teeth are fake

In a 2020 interview on the US talk show LIVE with Kelly and Ryan, Cryer remembered a troubling trip that the show had previously arranged for him.


On one occasion, the show sent him to Disney World Orlando, where Kelly recalled Cryer had “a little bit of a mishap.”

Upon his arrival, excited to try out the resort’s swimming pools, Cryer dived into the nearest option.


What Cryer hadn’t realised was that it was in fact a very shallow pool for children.

Colliding with the floor, he knocked out his two front teeth and was rushed off for medical treatment.


He had fake front teeth put in their place, and was ready for filming with the show the very next day.

18. He received death threats while starring in Two and a Half Men

Charlie Sheen, Jon Cryer’s Two and a Half Men co-star, was certainly more prominent in the news during his time on the show.


Still, his quieter co-star hit headlines in 2010 when he reported receiving death threats via the TV show’s own phone line.

Cryer suspected his ex-wife, Sarah Trigger, might be behind the menacing calls to the set.


The pair were embroiled in a messy custody battle over their son, Charlie Austin Cryer.

Sarah Trigger, who is a British actress, was reportedly interviewed by the FBI but never charged with anything.


Trigger and Cryer divorced back in 2004, just as Two and a Half Men was taking off. Coincidentally, Cryer’s co-star Charlie Sheen also got divorced in that year.

17. He’s played Lex Luthor in five different shows

So far, Superman’s nemesis Lex Luthor has been portrayed by Cryer in five TV series.


Since 2019, Cryer has appeared as Luthor in Arrow, The Flash, Legends of Tomorrow, Supergirl and Batwoman.

However, Cryer’s first-ever DC appearance dates all the way back to 1987, when he was directed by Sidney J. Furie.


Cryer played Lenny Luthor (Lex Luthor’s nephew) in the British-American movie Superman IV: The Quest For Peace.

Cryer has since said that Superman actor Christopher Reeve took him aside and warned him the movie was going to be “terrible.”


With a plot that made little sense, plus poor visual effects, Superman IV was indeed panned by critics, and it has often been described as one of the worst movies of all time.

16. Being mistaken for Matthew Broderick got him an acting career

Before Cryer became an actor, he was working as a theatre usher, and patrons often commented on how similar he looked to the star Matthew Broderick.


Enthused, Cryer decided to audition for Torch Song Trilogy, a Broadway show which was at the time seeking to replace Broderick.

Director Harvey Fierstein mistook him for Broderick when he first stepped out on stage, and Cryer won the role.


Later, Cryer became Broderick’s understudy in Brighton Beach Memoirs, a semi-autobiographical play by Neil Simon.

Cryer also took the lead in the romantic comedy No Small Affair when he was 19.


This part was originally meant to go to Broderick before the director fell ill and the initial production was cancelled.

15. He’s the Grand Marshal of an accessible playground

When his children were young, Cryer loved taking them to Shane’s Inspiration – an LA playground designed to be inclusive for disabled children.


He’s since campaigned and raised funds for the organisation behind the playground, so that similar playgrounds can be built internationally.

Shane’s Inspiration LA jokingly named Jon Cryer the Grand Marshal of the site, in recognition of his efforts.


“People the world over are realising this is something that is needed,” Cryer commented to Ability Magazine.

“But people weren’t thinking about this when they were building [these] places for children,” he explained.


Today, Shane’s Inspiration has created accessible playgrounds in nations including Russia, Ecuador and Israel.

14. Molly Ringwald and Andrew McCarthy found him “irritating”

In 2015, Cryer recorded in his memoir that Molly Ringwald was “irritated” with him “from day one” on the set of Pretty In Pink.


“Molly and Andrew were very reserved people, and I’m a very sociable person,” he added.

Andrew McCarthy was similarly annoyed by his 20-year-old co-star Cryer, who was three years his junior.


In a 2021 interview with news.com.au, McCarthy said the young Cryer had “a nervous laugh I found irritating.”

However, audiences clearly responded well to Cryer’s on-screen presence, which won him countless young female fans.


Speaking to the Daily News after the movie came out, Cryer’s mother Gretchen said she kept receiving giggling answer messages from fans on the family’s home phone.

13. He went to school with Robert Downey Jr and Erica Gimpel

Cryer is an alumnus of Junior High School 104 in New York City, with some serious stars-to-be in his midst.


These included Robert Downey Jr., Fame star Erica Gimpel and Kadeem Hardison of A Different World.

During casting for Pretty In Pink, Molly Ringwald was keen to recommend Robert Downey Jr. for the role of Duckie.


However, she’s since reflected to Vogue, “once Jon stepped into that role, there was no question that he was the guy.”

“He put so much of himself into that role that it’s impossible to imagine anybody else,” she added.


Robert Downey Jr. and Cryer ended up co-starring in 2010’s Due Date, where Downey plays a high-flying architect and Cryer has a cameo as his character Alan from Two and a Half Men.

12. He and Molly Ringwald disagree on whether Duckie from Pretty in Pink is gay

Jon Cryer’s breakthrough role was Duckie, the shy best friend in 1986’s Pretty in Pink.


Molly Ringwald, who took the female lead in this classic movie, has since commented to Out Magazine that she thinks the character Duckie is gay.

Cryer, however, has rebuffed this idea. Speaking to Zap2Itin 2012, he said of Ringwald’s claim, “I respectfully disagree.”


“I want to stand up for all the slightly effeminate dorks that are actually heterosexual,” Cryer clarified.

“Just ’cause the gaydar is going off, doesn’t mean your instruments aren’t faulty,” he stated.


“I’ve had to live with that, and that’s OK,” he said, referring to the tendency of many to assume Cryer himself is gay.

11. His ‘mother’ in the DC Universe is played by Brenda Strong, who’s only five years Cryer’s senior

In the CW series Supergirl, Cryer plays Lex Luthor – and his mother, Lillian Luthor, is played by Brenda Strong.


Born in 1965, Strong is a mere five years older than her on-screen son Cryer.

Meanwhile Lena Luthor, who is Lex Luthor’s paternal half-sister, is played by the Merlin star Katie McGrath.


McGrath is about two decades younger than Jon Cryer, and she has a more prominent role in this CW series.

In a 2019 interview with Entertainment Weekly, Cryer noted, “I felt like Lenny [Cryer’s Superman IV character] was a branch on the family tree that fell off pretty early and was rotting on the ground basically for a long while.”


“So I feel like [Supergirl] was my chance to sort of reclaim it and do it a little more justice, or injustice, as it were,” he commented.

10. He had a long run of failed TV shows before Two and a Half Men

Cryer worked hard to build a television career in the 90s and 00s – but his attempts were often unsuccessful.


He was in a long string of TV shows that were all cancelled, only ever lasting for one or two series.

These include The Famous Teddy Z, Partners, Getting Personal, The Trouble with Normal and Hey Joel.


Airing in 2003, Hey Joel was an adult animation about the journalist Joel Stein. Cryer provided the voice for the titular character.

Despite these failed shows, Cryer refused to become disheartened and he finally landed a lead role in what would become the hugely successful Two and a Half Men in 2003.


He secured seven Primetime Emmy Award nominations for his role in the show, as well as two wins.

9. He comes from a family of Broadway stars

Cryer was born in 1956 to David Cryer and Gretchen Kiger in New York City. His parents are veteran Broadway actors.


David is best known for playing Firmin in Phantom of the Opera and Juan Peron in Evita.

Credit: Ajay Suresh

In the latter role, Cryer’s father has racked up more performances than any other actor.


However, he started out in ministry before swapping to show business – and his own father was a Methodist minister.

Meanwhile Gretchen wrote and starred in a 1978 musical based on her own life, entitled I’m Getting My Act Together and Taking It on the Road.


Cryer decided at the age of 12 that he wanted to follow in his parents’ footsteps – to which his mother joked that plumbing might be a wise back-up plan.

8. Charlie Sheen described Cryer as “a turncoat, a traitor, a troll”

After Charlie Sheen was fired from Two and a Half Men, he and his co-star Cryer fell out of touch.


Sheen has since complained that Cryer failed to support him or look out for him during this difficult period.

Speaking to E! News in 2011, Sheen said: “When I’m starring in multimillion-dollar films and he’s begging me for a supporting role I’ll say, ‘You left me out in the cold.'”


“Like I said: You’re with me, or you’re with the trolls,” Sheen added. “Obviously he’s with the trolls.”

Sheen went on to describe Cryer as “a turncoat, a traitor, a troll. Clearly he’s a troll. He issued a statement [about me].”


“Is it gonna take me calling him a ‘traitor, juvenile and scared’ for him to get it?” Sheen asked. Cryer did not respond to these comments.

7. Sheen and Cryer co-starred in a movie over a decade before Two and a Half Men

Hot Shots! was a 1991 parody of Top Gun, and it starred both Cryer and his future Two and a Half Men co-star Charlie Sheen.


Sheen was in the lead role, playing Topper Harley, a pilot who is asked to return to the US Navy.

Jon Cryer plays LT Jim ‘Wash Out’ Pfaffenbach, one of the supporting characters who narrowly survives a plane accident.


This film was directed by Jim Abrahams, who’s also known for co-writing and co-directing 1980’s Airplane!

Hot Shots! became a huge commercial success, grossing more than $180 million worldwide on a budget of $26 million.


The friendship Cryer and Sheen built over the course of the movie was crucial in Cryer eventually securing a role in Two and a Half Men.

6. He once played the love interest of Two and a Half Men co-star Ashton Kutcher’s ex-wife Demi Moore

Cryer has mentioned that his on-screen history with Moore felt very strange when he raised it with his new co-star.


1984’s No Small Affair, a comedy-drama, sees a teenage Cryer star as an amateur photographer.

Released to mixed reviews, this movie has Cryer’s character fall in love with an older singer, played by Demi Moore.


Funnily enough, after Charlie Sheen’s departure from Two and a Half Men, Cryer was joined on the show by Ashton Kutcher – who was married to Demi Moore at the time.

Ashton and I have only really touched on that,” Cryer told the Hollywood Reporter in 2011.


“When I say his wife and I did a movie back when he was seven, it sounds vaguely like I’m trying to diminish him in some way,” he noted.

5. He was the only actor to feature in every single episode of Two and a Half Men

In the role of Alan Harper, Jon Cryer was a central figure in Two a Half Men for the entirety of its 12-year run.


Of the show’s first series, critic David Zurawik wrote in the Baltimore Sun: “The Sheen persona wears thin after a while, and Jones is just another kid actor with a goofy-sweet face. But what could make this sitcom fly is Cryer.”

In fact, Cryer was the only actor to appear in every single episode, after Sheen was replaced by Ashton Kutcher.


When the show came to a close in 2012, Kutcher took to Facebook to thank his four-year co-star.

“Thank you, Mr. Cryer, for making this job never feel like work,” Kutcher wrote. “I will miss working with you every day.”


“You are a true partner in every sense of the word,” he added of the Alan Harper actor.

4. His Two and a Half Men character once dressed up as Duckie

In the ninth season of Two and a Half Men, Cryer’s character Alan makes a sneaky reference to Pretty in Pink.


Reflecting on his youth, Alan jokes, “When I was in high school, I was dating a poster of Molly Ringwald.”

In Season 12, however, the references to Cryer’s Pretty in Pink character take an even stranger turn.


For a Halloween episode at the season’s start, Alan dresses up as Duckie from the classic film.

In an interview with Conan O’Brien, Cryer said, “you worry because it’s kind of sad when you see a famous teenage character and you realise, ‘Oh wait, they grew up!’”


“…But thankfully I could still get away with it, and it worked pretty well,” he added.

3. He got an ear piercing for 1987’s Dudes

In 1987, Cryer couldn’t wait for his first male lead role in the independent film Dudes.


He plays Grant, a punk caught up in a dramatic Western-style revenge plot after his friend is murdered.

Cryer learned how to fire a gun and ride a horse for the movie, and he even got an ear piercing to look the part.


He’s mentioned that he spent hours filming one scene in a freezing river, where he had to fish around for car keys.

But one critic for the New York Times felt that Cryer wasn’t very convincing as a punk rocker.


Describing the main characters as “self-consciously hip”, Janet Maslin noted that stars Jon Cryer and Daniel Roebuck “have a wholesomeness that doesn’t entirely suit their characters.”

2. He went to a specialist science high school

Before his acting career took off, the young Jon Cryer was clearly something of a brainiac.


As a teenager, Cryer attended one of the most prestigious and competitive schools in the USA.

He studied at the Bronx High School of Science, also known as Bronx Science, and he graduated in 1983.


Nowadays the school attracts about 30,000 applicants each year, all vying for about 900 places.

Aside from Cryer, its alumni include eight Nobel Prize winners and eight Pulitzer Prize winners.


Jon Favreau, Jonah Falcon and Dash Mihok were among the other show business stars to graduate from Bronx Science in the 80s.

1. He’s had a strangely similar life to actor Martin Lawrence

Jon Cryer and fellow sitcom actor Martin Lawrence were born on the exact same day: 16 April 1965.


Cryer was raised in New York City with his two sisters, while Lawrence was born in West Germany to a military family.

Both actors started out in NYC, with Cryer beginning his career on Broadway while Lawrence worked in comedy clubs.


Like Cryer, Lawrence ended up starring in sitcoms as well as Hollywood blockbusters, winning fame as an actor from the 90s onwards.

Lawrence starred in What’s Happening Now!, Martin, the Bad Boys movies and Big Momma’s House.

Two other famous actors to share this birthday are Charlie Chaplain and Claire Foy, born in 1889 and 1984 respectively.