Emmy Award winner, Jon Cryer, was born on April 16, 1965, in New York City. He's acted on Broadway, on TV and in film. On the silver screen, he's most recognized as the offbeat adolescent, Duckie, in the '80s classic "Pretty in Pink." He became an even bigger star as single parent Alan Harper on the sitcom "Two and a Half Men." The married actor is also a dad in real life.

Cryer was born into a showbiz family on April 16, 1965, in New York City. His parents, Gretchen and David Cryer, were actors who split when their son was 3. Cryer followed his mom and dad's footsteps into the spotlight at age 4 as a child model for a vitamin label. However, he didn't truly pursue acting until graduating from the Bronx High School of Science in 1983 and studying at the Royal Academy of Dramatic Art in London.

When Matthew Broderick stepped down from his role in the Broadway show "Torch Song Trilogy" in 1983, Cryer got his big break replacing him. The following year, he made his screen debut in the film "No Small Affair," about a teen photographer falling for an older woman, played by Demi Moore. In 1986, Cryer landed his landmark movie role as Duckie, a quirky high school student pining for his best friend, who was portrayed by Molly Ringwald, in John Hughes' "Pretty in Pink."

After his stint as the heartbroken Duckie character, Cryer worked in film consistently but got no major career boosts. Plus, there was a string of short-lived TV series like "The Fabulous Teddy Z," "Partners," "Getting Personal" and "The Trouble With Normal." (Supposedly, Cryer got an audition for the role of Chandler on Friends but couldn't make it due to scheduling conflicts.)

Finally, the sitcom "Two and a Half Men" came along in 2003 and was a big hit, boosting Cryer's acting credentials straight to the top. He plays Alan Harper, the uptight single dad of a young son, Jake (Angus T. Jones). In the show's early years, Cryer's character lived with his playboy brother, Charlie, played by Charlie Sheen. In 2011, Cryer became one of the targets of Sheen's public rants after the actor was fired. Sheen called his castmate a "troll" and a "traitor." Cryer took the high road in response and also took home the 2012 Emmy Award for Outstanding Lead Actor in a Comedy series. He'd already won a 2009 Best Supporting Actor in a Comedy Series award for the same role. (Ashton Kutcher subsequently replaced Sheen in "Two and a Half Men.")

"Two and a Half Men" signed off in February 2015 after twelve seasons. That April, Cryer published "So That Happened: A Memoir." The book included several interesting revelations. He wrote that he dated Demi Moore before his co-star Ashton Kutcher and hired a prostitute after his divorce from his first wife.

Besides acting and dabbling in screenwriting, producing and directing a few episodes of "Two and A Half Men," Cryer has plenty of other responsibilities in his role as a family man. Cryer has a son, Charles Austin, with ex Sarah Trigger, and a daughter, Daisy, whom he adopted in 2009 with his second wife, TV host/actress Lisa Joyner.

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