Before he became known as Alan Harper on the CBS hit series "Two and a Half Men," Jon Cryer was perhaps best known as Molly Ringwald's doting best friend Duckie in the 1986 film "Pretty in Pink."
Jonathan Niven Cryer was born to Broadway actors David and Gretchen Cryer, who must have passed along the acting gene to their son. He grew up acting and appeared in a commercial with his mother at age 4. Cryer went on to study the art at the prestigious summer acting camp Stagedoor Manor before being accepted into London's Royal Academy of Dramatic Art.
At age 19, the affable actor starred in the 1984 romance "No Small Affair" with Demi Moore and Jeffrey Tambor. He went on to “Pretty in Pink,” followed by the "Top Gun" parody "Hot Shots" (1991) with Cary Elwes and Charlie Sheen, who he would later appear with in "Two and a Half Men."
Cryer also worked on the independent films "The Pompatus of Love" and "Went to Coney Island on a Mission from God... Be Back by Five." He appeared in stage productions of "Brighton Beach Memoirs" on Broadway and "Torch Song Trilogy." He also starred in Howard Korder’s "Boy's Life" in Los Angeles in 1989 and "900 Oneonta" in London in 1994.
While in London, Cryer was asked to audition for "Friends" as sarcastic neighbor Chandler Bing, but his audition tape didn't make it back to the U.S. in time. The role went to Matthew Perry.
Still, the actor had accumulated numerous roles in such TV shows as "Getting Personal," "The Trouble With Normal," "Partners" and "The Famous Teddy Z" before landing the part of Alan Harper in "Two and a Half Men."
The situation comedy premiered in 2003 and cast Cryer in the role of conscientious single dad who, with his young son, moves into his playboy brother's Malibu home after a messy divorce. The sitcom became a hit and one of the decade's top-rated comedies.
In 2008, he appeared in "Tortured" with Laurence Fishburne and James Cromwell. The following year he costarred in "Shorts" with James Spader.
In 2009, he won the supporting actor in a comedy series Emmy for his role in the CBS series after being nominated for three consecutive years prior. He has directed numerous episodes of the series.
His character had a cameo appearance in the 2010 film "Due Date."