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In 2003, Cryer was cast as Alan Harper on the CBS sitcom Two and a Half Men, for which he won two Primetime Emmy Awards in 20.
Cryer received a star on the Hollywood Walk of Fame for Television in 2011.
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.
In 1993, he was asked to audition for the role of Chandler Bing on Friends, while doing a play in London. 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 2000, he was cast as the lead in a comedy series called The Trouble With Normal.This leads to the chief finding out that Marcus and Kevin have been impersonating Brittany and Tiffany. Later on, Kevin and Marcus find out that due to his bankruptcy Mr. Marcus apologizes to Gina, after realizing that being a female is a hard task, and because he had been ignoring Gina for his job.Vandergeld, along with Heath, has been behind the socialiate kidnappings in order to save himself and his family from poverty. Denise falls for Kevin, after Kevin saves her from a bullet.At the Hamptons hotel, Kevin and Marcus meet Brittany and Tiffany’s three best friends, Karen, Tori and Lisa, and their rivals Megan and Heather Vandegeld.They also encounter Karen’s abusive boyfriend, Heath, a broke, out of work actor.