Jon Cryer

Born in New York to parents who worked in show business, Jon Cryer made his professional acting debut in 1982, when he replaced fellow ’80s icon Matthew Broderick in the Broadway production of Torch Song Trilogy. His film debut came two years later, in the romantic comedy No Small Affair and became a household name after playing “Duckie” in the John Hughes classic Pretty in Pink.

Though he only starred in one of the director’s iconic teen movies, Cryer has long been associated with the “Brat Pack,” the group of highly successful young actors who frequently worked together throughout the decade.

After guest spots on TV shows like Dharma & Greg and starring in multiple failed pilots, Cryer rocketed to a new level of fame in 2003, when he was cast opposite Charlie Sheen in Two and a Half Men. He earned seven Primetime Emmy Awards nominations for his performance as neurotic, recently divorce Alan Harper, taking home the trophy in 2009 and 2012. In the wake of Sheen’s 2011 departure from the show amid a highly public drug battle, Cryer became the leading man on the hit sitcom. He was joined by Ashton Kutcher for the sitcom’s remaining three seasons.

In 2015 Cryer released his memoir, So That Happened, which chronicled his decades-long career on stage and screen. He has also played key roles on NCIS, Supergirl and The Flash.

Cryer married British actress Sarah Trigger in 1999 and they welcomed son Charlie one year later. The pair called it quits in 2004. Three years later, Cryer married entertainment reporter Lisa Joyner and they adopted a baby girl in September 2009.