Most of us first met Jon Cryer as Phil “Duckie” Dale in Pretty in Pink. He was just 19 when he landed that role. It took several failed TV series before Cryer landed another big score. In 2003 he was cast as Alan Harper in Two and a Half Men, a role he was apparantly born to play. Jon has been nominated for seven Primetime Emmy Awards and won two of them. The show remains a ratings winner. Jon Cryer turns 48 today.