Dark-haired comedic actor Jon Cryer remains best-known for his lovable performance as Duckie Dale in the 1986 teen movie Pretty in Pink. Even though he was 21 years old playing a high school senior, he exhibited a vulnerable yet goofy freshness unlike most other teen stars. The son of Broadway performers, he was schooled in the Bronx before making his film debut in the romantic comedy No Small Affair as a young photographer obsessed with Demi Moore. He made some unfortunate movies after Pretty in Pink, including the Ferris Bueller knock-off Morgan Stewart's Coming Home, which suggested unfair comparisons with actor Matthew Broderick. Other forgettable movies followed until he was cast as the star of the sitcom The Famous Teddy Z, which was then followed by several other short-lived sitcoms. After appearing in the anarchic comedy Hot Shots!, he proved fairly successful with offbeat comedies and independent films. He helped write the talky romantic comedy The Pompatus of Love then starred in the similarly themed Plan B. He teamed up with director Richard Schenkman to write the offbeat comedy Went to Coney Island on a Mission From God...Be Back by Five.
In 2003, Cryer re-teamed with Hotshots! co-star Charlie Sheen for the sitcom Two and a Half Men, which proved to be a massive success. The show was so popular that it stayed on the air, even after Sheen left in 2011, with Ashton Kutcher filling in the empty spot in the cast.