The son of Broadway performers David and Gretchen Cryer, Jon Cryer was indoctrinated into showbiz at a young age as a child model and stage performer. Although his early success as Molly Ringwald's manic buddy Duckie in Pretty in Pink seemed to imply a wonderful future, his career stalled after a series of forgettable films. In the '90s Cryer wisely focused almost solely on television. Although four of his sitcoms flopped, he remained undaunted, and in 2003 he finally scored a hit as a pent-up single father on Two and a Half Men. That role earned him Emmy nominations four years in a row, and he finally won for Outstanding Supporting Actor in a Comedy Series in 2009.