Jon Cryer has been a known face on the acting scene for a very long time, but he became a real superstar to worldwide audiences when he starred as Alan Harper in the sitcom Two and a Half Men, alongside Charlie Sheen.

Cryer and Sheen became great friends on the set, but they also underwent some thought times, including Sheen being fired. Jon also got a divorce, and has even revealed since that he once paid for s*x.

However, today, the Walk of Fame-honored actor has found love again, and has children. Interestingly, his now-wife initially thought he was gay when they first met, and that Cryer was destined to become her “gay friend.”

This is all you need to know about Jon Cryer!

Every actor and actress searches ceaselessly for their big breakthrough. For some, these breakthroughs come at a very early age, while others are forced to fight their way through the entertainment business, hoping to score that one significant role in a film, television series, or in theater.

For actor Jon Cryer, the most prominent role of his life thus far came after a series of rocky years. He starred in many television shows, but virtually all of them had flopped.

The failures took their toll on him, while many of his critics thought that he just wasn’t destined to reach the upper-echelons of on-screen stardom.

Jon Cryer – early life in New York

It was at that point that he scored the role of Alan Harper in Two and a Half Men. He starred alongside Charlie Sheen, and the show made him a worldwide star.

Since the start of the now-classic sitcom, Cryer’s life has changed very much. He’s been through a divorce, remarried, and even welcomed children.

So how did he get there in the first place?

Jon Cryer was born on April 16, 1965, in New York City. Both of his parents, mother Gretchen Cryer and father David Cryer, worked as actors. One might say that Jon was born for the stage.

“I was born on a Friday night at 8:15 – 15 minutes after showtime. And my mom is a playwright, so I grew up in that world,” Cryer told Ability Magazine.

“I knew pretty much, from when I was eight or nine years old, that this is what I wanted to do, just because it’s so stupid, it’s such a silly job. I kind of can’t believe people get paid for it.”

Cryer got to hang out backstage at both on and off-Broadway theaters, and his father was actually in a production called The Fantasticks, which ran off-Broadway for more than 30 years.

“When you’re a little kid, and you’re backstage seeing all these crazy, magical people floating in and out of your life, it can’t help but cast a spell on you,” he said.

“I wanted to be a part of that.”

“It was this or nothing”

At first, Cryer fell in love with the theater. At the same time, however, he loved movies, and from the age of seven, he recalled that he watched pretty much every television show going.

When Jon was four years of age, his parents divorced, and his mother assumed custody. She worked as both an actress and writer, and made sure that her son joined her at work. That led to his first job in acting, as he appeared alongside his mother in a television commercial for vitamins.

Jon was hooked, and decided to pursue a career in the entertainment business. He got his first job as an usher – the person who usually welcomes and shows people where to sit – and later as a house manager, a job that entailed him cleaning toilets.

Now, it should go without saying that the entertainment industry, especially in New York, is very competitive. Cryer learned early on that acting wasn’t necessarily something one could make a living out of.

“But of course, many people do it and don’t get paid. That was something I learned later. But at any rate, I went to a theater camp in upstate New York and was doing 18 musicals a summer,” he said.

“It was one of those things where I never gave myself another option. I never really had anything to fall back on. It was this or nothing.”

“But I didn’t give myself an alternative,” Cryer added.

“And I also got incredibly lucky because when I was about 17 or 18, there was a huge burst of teen movies and lots of parts for people my age. You can’t bank on that.

Jon Cryer – big breakthrough in ‘Pretty in Pink’

“But I just got lucky. So I started working when I was 18 got my first couple of jobs. My first gig was as Matthew Broderick’s understudy in Brighton Beach Memoirs; I lasted six weeks before they fired me.”

Instead of going to college, Cryer put everything he had into one basket: to try and make it as an actor. He went to study at the Royal Academy of Dramatic Arts in London, appeared in some productions, and made guest appearances on television.

Then, in 1986, at the age of 21, Cryer got his first breakthrough, as he starred alongside Molly Ringwald in the film Pretty in Pink. At that point, Jon had already made his debut on Broadway in the production Torch Song Trilogy, which brought him to Los Angeles, where move television and film jobs appeared.

He starred as Phillip Dale, also known as “Duckie,” in Pretty in Pink. It became a role of great importance for him, and not only because of its significance for his career.

“Duckie was the guy I wanted to be in high school,” he explained. “I was a theater geek at a science geek school. So I did not fit in. I wore leg warmers. I’m not proud of it! I wish that I had been as extroverted and sure of myself as Duckie was. But that was not me.”

Cryer was on the way up in his acting career, though the following years were a real struggle. First, Cryer landed the lead in the television series comedy The Famous Teddy Z, but the show only lasted for 20 episodes. After that, he landed roles in series such as PartnersGetting PersonalThe Trouble With Normal.

All of them were canceled.

Was considered a “show killer”

Cryer was even labeled a “show killer” by Newsweek. Of course, as many actors before and after him can testify, show business is a very harsh climate indeed. One day, someone’s a superstar; the next day, a nobody or a has-been.

For Cryer, the lack of jobs was a problem.

“After the ‘show killer’ thing — I joke about it now, but at the time, it was a real issue for me in the industry,” Cryer recalled.

“There was not a lot of people that wanted to hire me for a while. I spent three years with very little work.”

Fortunately, in 2003, everything changed when Cryer went to audition for a new sitcom called Two and a Half Men. Network CBS was unhappy that the series creator, Chuck Lorre, wanted Cryer for the part of Alan Harper. They believed him to be a nobody, and didn’t see him as the right fit.

“I knew his work, and I was kind of disappointed that they didn’t want to meet or even see him,” Lorre said. “But his representatives said, ‘you really should see him for this part.’ So there was nothing in that conversation with CBS keeping me from seeing him. So he read for the part, and he was brilliant. Clearly heads and shoulders above anyone else trying out for the part. It was perfect.”

How Jon Cryer got the part of Alan Harper in ‘Two and a Half Men’

However, there was one big obstacle: CBS’s head of casting didn’t want anything to do with him. Chuck was supposed to be bringing his choices for the parts in Two and a Half Men, and so he called the head of casting at CBS.

“You’re bringing Cryer, aren’t you,” Lorre recalled the head of casting saying.

“He came in and read in the worst possible circumstance. They really didn’t want to like him. But he was brilliant. It was the right choice. He has never been anything other than brilliant on the show every week. He is one of the great actors of our time,” he added.

Cryer starred alongside Charlie Sheen – whom he had worked with on the comedy film Hot Shots – and Angus T. Jones, who starred as Jake Harper. The show became a massive success, and today, it’s seen as one of the great sitcoms. Cryer stayed on the show for a total of 12 years, appearing in 262 episodes.

Cryer turned into a worldwide superstar thanks to his portrayal of Alan – it even earned him a star on the Hollywood Walk of Fame. He also became the first man ever to win both a Primetime Emmy for Best Actor and Best Supporting Actor for the same show.

Relationship with Charlie Sheen

However, the show had plenty of drama going on behind the scenes, with Charlie Sheen being fired in 2011, calling Cryer a “turncoat, a traitor, a troll.”

“At the time, I was not angry [with Charlie Sheen],” Cryer said. “I was just scared every day that I was going to read about Charlie being dead. But anybody who has gotten close to him knows that there’s a really great guy in there. And that he’s been a guy going through some very tough times. And you just have to feel for somebody going through that.”

Charlie and Jon didn’t speak for years. Then, in 2015, they finally met up, and Sheen apologized.

“It was great to see him after all of the craziness because we did have something great together,” Cryer reminisced.

“I don’t know. I loved working with him before, but I don’t know how much I can invite that into my life at this point! We’ll see. But I’ll never say never.”

Throughout the 2000s, Two and a Half Men became a considerable part of Cryer’s life. At the same time, he experienced a lot in his personal life.

In 1999, he married his first wife, Sarah Trigger. They welcomed son Charlie Austin Cryer in 2000, though the couple then divorced in 2004.

Jon Cryer – marriage, wife, children

At that point, Cryer was lost. The divorce broke his heart, and he felt “undatable.” He revealed in his memoir (as per the Hollywood Reporter) that he even went as far as paying for sex.

“I was in a bad state right after my divorce, and I certainly didn’t feel dateable. I was an emotional basket case. What good was I to any woman I might have interest in? I decided I might as well pay someone for company and certain intimate pleasures so that I could at least get my equilibrium back with the opposite sex,” Cryer wrote.

Charlie Sheen suggested a “few online purveyors,” and Cryer decided to go for it. He wrote that his first experience was “as awkward as you might imagine.”

“It was really a very friendly experience, maybe because the act of having sex is quite the conversational icebreaker. The next time, I went to her place, which probably wasn’t really her place,” Cryer wrote.

“We sat down, tried to make small talk, and halfheartedly stumbled into a conversation about recent fluctuations in the stock market. Somehow I ended up spending 25 minutes of my hour helping her with financial planning.”

As the big success with Two and a Half Men continued, Cryer met and wed his second wife, television host, actress, and producer Lisa Joyner.