Jon Cryer is an American actor with a Hollywood career spanning decades. He debuted in the 1984 film No Small Affair. He next gained recognition for starring as Phil “Duckie” Dale in the romantic comedy movie Pretty in Pink. Meanwhile, his first starring role on television was as Teddy Zakalokis on The Famous Teddy Z. He next starred as Bob on the sitcom Partners. In the 2000s, he starred as Zack Mango on the short-lived series The Trouble with Normal. It was, however, his role as Alan Harper on the sitcom Two and a Half Men that made a television staple. For his work here, he won two Primetime Emmys – one for Outstanding Supporting Actor and one for Outstanding Lead Actor.