Jon Cryer became a worldwide star thanks to his work on the television series Two and a Half Men, where he starred alongside Charlie Sheen as Alan Harper.

The actor had his big breakthrough at the age of 21, in the 1986 film Pretty in Pink, but that wasn’t the first time he had stood in front of a Hollywood camera.

In 1984, Cryer starred in the film No Small Affair, alongside Demi Moore; his first big production. The actors reportedly not only became working colleagues, but also engaged in a romantic affair.

Cryer turned out to be more in love with Demi Moore than she was in love with him, and their romance didn’t last for long. Years later, in her 2019 memoir, Moore revealed that she had taken his virginity. However, Cryer denied this was remotely close to being accurate, and revealed other details about the actress and their relationship.

Here’s all you need to know about Moore and Cryer’s love affair.

Before Jon Cryer turned into a star on the sitcom Two and a Half Men, he had actually already had a long and successful acting career. Plainly put, it wasn’t Two and a Half Men that made him a brilliant and celebrated actor, though the sitcom was undeniably his most prominent role yet.

As it happens, many of his critics doubted that he was destined to reach the upper echelons of on-screen stardom.

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

“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,” he explained.

“I kind of can’t believe people get paid for it.”

Cryer got to hang out backstage at 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.”

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 watching pretty much every television show going.

When Jon was four years of age, his parents divorced, and his mother assumed custody of Jon. 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.

“It was this or nothing”
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 position that involved him cleaning toilets.

It should go without saying that the entertainment industry, especially in New York, is very competitive. As a result, Cryer learned early on that acting wasn’t necessarily something one could make a living out of. But still, the up-and-coming actor, passionate about the art of performing in front of the camera, didn’t care about the money.

“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 said.

“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,” he added.

“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.”

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