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Jon Cryer make his big break through on the big screen as Duckie in the 1980s John Hughes classic, Pretty in Pink.  However, Cryer definitely became a household name for his role as Charlie’s nerdy brother, Alan, in Two and a Half Men.  He won an Emmy for the role in 2009.

By Sara Trimble

When a reporter branded a group of young actors as the Brat Pack, it caused a wave of typecasting that left ripples on their careers for years.