Career
Cryer's first professional acting effort was as David in the Broadway play Torch Song Trilogy, replacing Matthew Broderick, who he closely resembled. Jon later was an understudy and replacement for Broderick in Neil Simon's Brighton Beach Memoirs in 1989. This resemblance became something of a running joke, even referenced numerous times on his later hit series Two and a Half Men, where his character posed as Broderick in order to get star treatment, on numerous occasions.
At age 19, Cryer appeared in the 1984 romantic comedy film No Small Affair, in the lead role as Charles Cummings. He went on to have small roles in films and television movies, and he made his breakthrough as Phil "Duckie" Dale in the John Hughes-scripted film Pretty in Pink. In an interview with the Daily News, Cryer's mother said that after Pretty in Pink, she started getting calls from teenage girls from all over the world, who would leave hysterical, giggling messages on her answering machine. Thanks to Pretty in Pink, Cryer slowly became more famous. In 1989, he got the lead role in the TV comedy series, The Famous Teddy Z. His performance gained poor reviews and the show was canceled after the first season.
One year later, he starred with Charlie Sheen in the Jim Abrahams comedy Hot Shots!, which was received very positively. Cryer is frequently linked to the Brat Pack. In a March 2009 interview on Anytime with Bob Kushell, Cryer stated that he had auditioned for St. Elmo's Fire but was not cast in a role. In 1993, he was asked to audition for the role of Chandler Bing on Friends, while doing a play in London. His reading was videotaped by a British casting agent but the tape failed to arrive in the U.S. before the network had made its final decision.
In 1995, he was cast as Bob in the sitcom Partners, which, like his prior show The Famous Teddy Z, was canceled after its first season. In an interview with Time Out New York he stated, "Hey, every show I'm in goes down. Think about this: George Clooney was in 28 pilots, or something. It means nothing". After guest starring on shows such as Dharma & Greg and The Outer Limits, he successfully wrote and produced the film, Went to Coney Island on a Mission from God... Be Back by Five. It debuted in 1998 at the Los Angeles Film Festival and gained positive reviews from critics. Leonard Maltin from Playboy Magazine called it "A breath of fresh air". In 2000, he was cast as the lead in a comedy series called Trouble With Normal. For the third time, Cryer starred in a show which was canceled after its first season.
Cryer's long run of unsuccessful TV projects finally ended three years later. Against the wishes of CBS executives (who were aware of his past failures), he was cast in 2003 to portray Alan Harper on the hit comedy series Two and a Half Men. To date, he has earned seven Primetime Emmy Award nominations and two wins for his acting work on the show.. In a comment on the show's high ratings, he said, "When you’re on a show that's fighting for survival every week, you stop trusting your instincts, because you think, ‘My instincts haven't worked so far.’ But when people clearly like the show and are watching it in great numbers, it takes a huge amount of pressure off you. It allows you to trust your instincts and go with what has worked for you before." Before being cast for Two and a Half Men, Cryer auditioned for the role of Gaius Baltar on the Sci-Fi Channel's reimagined Battlestar Galactica, but the role went to James Callis. In 2008, Cryer appeared with Laurence Fishburne and James Cromwell in the film Tortured, and in 2009 co-starred with James Spader in the film Shorts.
Cryer made a guest appearance on the sitcom series Husbands in its second season.
He will voice the lead character in the upcoming direct to video Disney animation Planes, a spin-off of Pixar's Cars.
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